Giordaina and Tom Downes attended the Oxford Synthesis Summer Conference on 25-26 June. Giordaina presented a poster on her MSc research entitled ”α-Functionalisation of Cyclic Sulfoximines: Scope and Diastereoselectivity” and Tom gave a poster on the 3-D Fragments projects in the group. Tom also gave a well-received flash presentation entitled “Design and Synthesis of a 3-D Fragment Library”.
Peter O'Brien studied for a degree and PhD at the University of Cambridge. He carried out a PhD supervised by Stuart Warren on chiral phosphine oxides. After the award of his PhD in 1995, he moved to the University of York as a Royal Commission for the Exhibition of 1851 Research Fellow, hosted in the laboratory of Professor R. J. K. Taylor. In March 1996, he was appointed as a lecturer in organic chemistry at The University of York. In 1999, he was awarded one of the Royal Society of Chemistry's Meldola medals and prizes and in 2000, a GlaxoWellcome award for innovative organic chemistry. He was promoted to Senior Lecturer (2002), Reader (2005) and Professor (2007). He was awarded the Royal Society of Chemistry's Organic Stereochemistry Award in 2013 and a Vice-Chancellor’s Teaching Award for 2014-15.
The O’Brien group’s research focuses on contemporary organic synthesis, with a particular interest in asymmetric synthesis. Current research projects are focused in three areas:
Peter O'Brien receives the Meldola Medal from Tony Ledwith, President of the RSC
Hon Eong Ho, Thomas C. Stephens , Thomas J. Payne, Peter O’Brien , Richard J. K. Taylor, and William P. Unsworth. ACS Catal., 2019, 9, 504-510
James D. Firth and Peter O'Brien. Chemical and Biological Synthesis: Enabling Approaches for Understanding Biology, 2018, pp. 74-113 DOI: 10.1039/9781788012805-00074
137. "A Synthetic and Spectroscopic Investigation of the Asymmetric α-Lithiation-trapping of Six-Membered N-Boc Heterocycles using Alexakis Diamines"
James D. Firth, Giacomo Gelardi, Peter J. Rayner, Darren Stead, and Peter O'Brien. Heterocycles. 2018, DOI: 10.3987/COM-18-S(T)87
Hon Eong Ho, Michael J. James, Peter O’Brien , Richard J. K. Taylor, and William P. Unsworth. Org. Lett. 2018, 20, 1439–1443
James D. Firth, Steven J. Canipa, Leigh Ferris, Peter O'Brien. Angew. Chem. Int. Ed. 2018, 57, 223-226
John F. Darby, Masakazu Atobe, James D. Firth, Paul Bond, Gideon J. Davies, Peter O'Brien and Roderick E. Hubbard, Chem. Sci., 2017, 8, 7772-7779
J. D. Firth, P. O’Brien and L. Ferris, J. Org. Chem., 2017, 82, 7023–7031
M. J. James, N. D. Grant, P. O’Brien, R. J. K. Taylor and W. P. Unsworth, Org. Lett. 2016, 18, 6256-6259.
A. K. Clarke, M. J. James, P. O'Brien, R. J. K. Taylor and W. P. Unsworth, Angew. Chem. Int. Ed. 2016, 55, 13798-13802.
M. J. James, P. O'Brien, R. J. K. Taylor and W. P. Unsworth, Angew. Chem. Int. Ed. 2016, 55, 9671-9675.
J. T. R. Liddon, M. J. James, A. K. Clarke, P. O'Brien, R. J. K. Taylor and W. P. Unsworth, Chem. Eur. J. 2016, 22, 8777-8780.
S. J. Chambers, G. Coulthard, W. P. Unsworth, P. O'Brien and R. J. K. Taylor, Chem. Eur. J, 2016, 22, 6496-6500
J. D. Firth, P. O’Brien and L. Ferris, J. Am. Chem. Soc., 2016, 138, 651-659.
M. J. James, P. O’Brien, R. J. K. Taylor and W. P. Unsworth, Chem. Eur. J. 2016, 22, 2856-2881.
P. J. Rayner, J. C. Smith, C. Denneval, P. O’Brien, P. A. Clarke and R. A. J. Horan, Chem. Commun. 2016, 52, 1354-1357.
124 “Silver(I)-Catalysed Dearomatisation of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles”
M. J. James, R. E. Clubley, K. Y. Palate, T. J. Procter, A. C. Wyton, P. O’Brien, R. J. K. Taylor and W. P. Unsworth, Org. Lett., 2015, 17, 4372-4375.
123 “Investigation of the Lithiation-trapping of a N-Boc Bispidine-ketal: Reactivity and Diastereoselectivity”
D. Stead, P. O’Brien and A. Sanderson, Synlett, 2015, 26, 2381-2384.
122 “Silver(I) or copper(II)-mediated dearomatisation of aromatic ynones: direct access to spirocyclic scaffolds”
M. J. James, J. D. Cuthbertson, P. O’Brien, R. J. K. Taylor and W. P. Unsworth, Angew. Chem. Int. Ed., 2015, 54, 7640-7643.
121 “Lead-oriented synthesis: investigation of organolithium-mediated routes to 3-D scaffolds and 3-D shape analysis of a virtual lead-like library”
M. Lüthy, M. C. Wheldon, C. Haji-Cheteh, M. Atobe, P. S. Bond, P. O’Brien,R. E. Hubbard and I. J. S. Fairlamb, Bioorg. Med. Chem., 2015, 23, 2680-2694.
120 “Cross-Coupling Knows No Limits: Assessing the Synthetic Potential of the Palladium-Catalysed Cross-Coupling of Organolithiums”
J. D. Firth and P. O’Brien, ChemCatChem, 2015, 7, 395-397.
119 “Revisiting the sparteine surrogate: development of a resolution route to the (–)-sparteine surrogate”
J. D. Firth, P. O’Brien and L. Ferris, Org. Biomol. Chem. 2014, 12, 9357-9365.
118 “Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: comparison of (–)-sparteine and (+)-sparteine surrogates”
S. J. Canipa, A. Stute and P. O’Brien, Tetrahedron, 2014, 70, 7395-7403.
117 “On the synthesis of a-amino sulfoxides”
P. J. Rayner, G. Gelardi, P. O’Brien, R. A. J. Horan and D. C. Blakemore, Org. Biomol. Chem. 2014, 12, 3499-3512.
116 “Asymmetric Lithiation-Trapping of N-Boc Heterocycles at Temperatures above –78 °C”
G. Gelardi, G. Barker, P. O’Brien and D. C. Blakemore, Org. Lett. 2013, 15, 5424-5427.
115 “Preparation and Reactions of Enantiomerically Pure a-Functionalised Grignard Reagents”
P. J. Rayner, P. O’Brien and R. J. Horan, J. Am. Chem. Soc. 2013, 135, 8071-8077.
114 “Halogen-Bonded Liquid Crystals of 4-Alkoxystilbazoles with Molecular Iodine: a Very Short Halogen Bond and Unusual Mesophase Stability”
L. J. McAllister, C. Präsang, J. P.-W. Wong, R. J. Thatcher, A. C. Whitwood, B. Donnio, P. O'Brien, P. B. Karadakov and D. W. Bruce, Chem. Commun. 2013, 49, 3946-3948.
113 “Stereocontrolled Synthesis of the AB Rings of Samaderine C”
D. J. Burns, S. Mommer, P. O’Brien, R. J. K. Taylor, A. C. Whitwood, and S. Hachisu, Org. Lett., 2013, 15, 394-397.
112 “Synthesis of P-Stereogenic Phospholene Boranes via Asymmetric Deprotonation and Ring-Closing Metathesis”
X. Wu, P. O’Brien, S. Ellwood, F. Secci and B. Kelly, Org. Lett., 2013, 15, 192-195.
111 “Amines bearing tertiary substituents by tandem enantioselective carbolithiation–rearrangement of vinyl ureas”
M. Tait, M. Donnard, A. Minassi, J. Lefranc, B. Bechi, G. Carbone, P. O’Brien and J. Clayden, Org. Lett., 2013, 15, 34-37.
110 “Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis”
D. J. Burns, S. Hachisu, P. O’Brien and R. J. K. Taylor, Org. Biomol. Chem., 2012, 10, 7666-7668.
109 “An Experimental and In Situ IR Spectroscopic Study of the Lithiation–Substitution of N-Boc 2-phenylpyrrolidine and piperidine: Controlling the Formation of Quaternary Stereocenters”
N. S. Sheikh, D. Leonori, G. Barker, J. D. Firth, K. R. Campos, P. O’Brien and I. Coldham, J. Am. Chem. Soc., 2012, 134, 5300-5308.
108 “Enantioselective, Palladium-Catalyzed a-Arylation of N-Boc Pyrrolidine: In Situ React IR Spectroscopic Monitoring, Scope and Synthetic Applications”
G. Barker, J. L. McGrath, A. Klapars, D. Stead, G. Zhou, K. R. Campos and P. O’Brien, J. Org. Chem. 2011, 76, 5936-5953.
107 “One-ligand Catalytic Asymmetric Deprotonation of a Phosphine Borane: Synthesis of P-Stereogenic Bisphosphine Ligands”
J. Granander, F. Secci, S. J. Canipa, P. O’Brien and B. Kelly, J. Org. Chem. 2011, 76, 4794-4799.
106 “Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-OMethylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization”
A. R. Germain, D. M. Bruggemeyer, J. Zhu, C. Genet, P. O’Brien and J. A. Porco, Jr., J. Org. Chem. 2011, 76, 2577-2584.
105 “Investigation of bispidines as the stoichiometric ligand in the two-ligand catalytic asymmetric deprotonation of N-Boc pyrrolidine”
G. Barker, P. O’Brien and K. R. Campos, ARKIVOC 2011, (v), 217-229.
104 “Asymmetric Deprotonation using s-BuLi or i-PrLi and Chiral Diamines in THF: the Diamine Matters”
G. Carbone, P. O’Brien and G. Hilmersson, J. Am. Chem. Soc., 2010, 132, 15445-15450.
103 “Synthesis of P-Stereogenic Compounds via Kinetic Deprotonation and Dynamic Thermodynamic Resolution of Phosphine Sulfides: Opposite Sense of Induction using (–)-Sparteine”
J. J. Gammon, V. H. Gessner, G. R. Barker, J. Granander, A. C. Whitwood, C. Strohmann, P. O’Brien and B. Kelly, J. Am. Chem. Soc., 2010, 132, 13922-13927.
102 “Diamine-free Lithiation-Trapping of N-Boc Heterocycles using s-BuLi in THF”
G. Barker, P. O’Brien and K. R. Campos, Org. Lett. 2010, 12, 4176-4179.
101 “Asymmetric Synthesis via Aziridinium Ions: Exploring the Stereospecificity of the Ring Opening of Aziridinium Ions and a Formal Synthesis of (–)-Swainsonine”
S. J. Oxenford, S. P. Moore, G. Carbone, G. Barker, P. O’Brien, M. R. Shipton, J. Gilday and K. R. Campos, Tetrahedron: Asymmetry, 2010, 21, 1563-1568.
100 “Asymmetric Deprotonation of N-Boc Piperidine: React IR Monitoring and Mechanistic Aspects”
D. Stead, G. Carbone, P. O’Brien, K. R. Campos, I. Coldham and A. Sanderson, J. Am. Chem. Soc., 2010, 132, 7260-7261.
99 “Unexpected products from the attempted organolithium-mediated conversion of cyclic β-methoxy aziridines into allylic amines”
S. C. Coote and P.O’Brien, Tetrahedron Lett., 2010, 51, 588-590.
98 “Kinetic Resolution of P-Stereogenic Phosphine Boranes via Deprotonation using s-Butyllithium/(–)-sparteine”
J. Granander, F. Secci, P. O’Brien and B. Kelly, Tetrahedron: Asymmetry, 2009, 20, 2432-2434.
97 “Catalytic Asymmetric Deprotonation of a Phosphine Borane: Comparison of Two-ligand and One-ligand Catalysis”
S. J. Canipa, P. O’Brien and S. Taylor, Tetrahedron: Asymmetry, 2009, 20, 2407-2412.
96 “Regioselective Lithiation of Silyl Phosphine Sulfides: Asymmetric Synthesis of P-Stereogenic Compounds”
J. J. Gammon, P. O’Brien and B. Kelly, Org. Lett., 2009, 11, 5022-5025.
95 “Catalytic Asymmetric Synthesis of Piperidines from Pyrrolidine: Concise Synthesis of (+)-L-733,060”
J. L. Bilke, S. P. Moore, P. O’Brien and J. Gilday, Org. Lett., 2009, 11, 1935-1938.
94 “Lithiation-Electrophilic Trapping of N-Sulfonyl-activated Ethylene Aziridines”
J. Huang, S. P Moore, P. O’Brien, A. C Whitwood and J. Gilday, Org. Biomol. Chem., 2009, 7, 335.
93 “Stereoselective Aziridination of Cyclic Allylic Alcohols Using Chloramine-T”
S. C. Coote, P. O’Brien and A. C. Whitwood, Org. Biomol. Chem., 2008, 6, 4299-4314.
92 “Organolithium-mediated Conversion of b-Alkoxy Aziridines into Allylic Sulfonamides: Effect of the N-Sulfonyl Group and a Formal Synthesis of (±)-Perhydrohistrionicotoxin”
S. C. Coote, S. P. Moore, P. O’Brien, A. C. Whitwood and J. Gilday, J. Org. Chem., 2008, 73, 7852-7855.
91 “On the Two-Ligand Catalytic Asymmetric Deprotonation of N-Boc Pyrrolidine: Probing the Effect of the Stoichiometric Ligand”
J. L. Bilke and P.O’Brien, J. Org. Chem., 2008, 73, 6452-6454.
90 “Catalytic Asymmetric Deprotonation of Phosphine Boranes and Sulfides as a Route to P-Stereogenic Compounds”
J. J. Gammon, S. J. Canipa, P. O’Brien, B. Kelly and S. Taylor, Chem. Commun. 2008, 3750-3752.
89 “Palladium-Catalyzed Enantioselective Oxidation of Chiral Secondary Alcohols: Access to Both Enantiomeric Series”
D. C. Ebner, R. M. Trend, C. Genet, M. J. McGrath, P. O'Brien and B. M. Stoltz, Angew. Chem. Int. Ed. 2008, 47, 6367-6370.
88 “Expanding the Synthetic Potential of Asymmetric Deprotonation: Arylation of Carbanions”
P. O’Brien and J. L. Bilke, Angew. Chem. Int. Ed. 2008, 47, 2734-2736.
87 “Basic Instinct: Design, Synthesis and Evaluation of (+)-Sparteine Surrogates for Asymmetric Synthesis”
P. O’Brien, Chem. Commun., 2008, 655-667. (Feature Article)
86 “A New Sparteine Surrogate for Asymmetric Deprotonation of N-Boc Pyrrolidine”
D. Stead, P. O’Brien and A. Sanderson, Org. Lett. 2008, 10, 1409-1412.
85 “Synthesis of Substituted Allylic Sulfonamides from b-Alkoxy Aziridines and Organolithium Reagents”
S. P. Moore, P. O’Brien, A. C. Whitwood and J. Gilday, Synlett 2008, 237-241.
84 “Stereocontrolled Synthesis and Alkylation of Cyclic b-Amino Esters: Asymmetric Synthesis of a (–)-Sparteine Surrogate”
J-P. R. Hermet, A. Viterisi, J. M. Wright, M. J. McGrath, P. O’Brien, A. C. Whitwood and J. Gilday, Org. Biomol. Chem., 2007, 5, 3614-3622.
83 “Total synthesis of the lupin alkaloid cytisine: comparison of synthetic strategies and routes”
D. Stead and P. O’Brien, Tetrahedron, 2007, 63, 1885-1897.
82 “Asymmetric deprotonation of N-Boc piperidines”
I. Coldham, P. O’Brien, J. J. Patel, S. Raimbault, A. J. Sanderson, D. Stead and D. T. E. Whittaker, Tetrahedron: Asymmetry, 2007, 18, 2113-2119.
81 “New route to azaspirocycles via the organolithium-mediated conversion of b-alkoxy aziridines into cyclopentenyl amines”
S. P. Moore, S. C. Coote, P. O’Brien and J. Gilday, Org. Lett. 2006, 8, 5145-5148.
80 “Synthesis of (+)-(1R,2S,9S)-11-Methyl-7,11-Diazatricyclo[7.3.1.02,7]tridecane, a (+)-Sparteine Surrogate”
A. J. Dixon, M. J. McGrath and P. O’Brien, Org. Synth., 2006, 83, 141-154.
79 “Catalytic Asymmetric Synthesis of Ferrocenes and P-Stereogenic Bisphosphines”
C. Genet, S. J. Canipa, P. O’Brien and S. Taylor, J. Am. Chem. Soc., 2006, 128, 9336-9337.
78 “Development of a Catalytic Asymmetric Variant of Hoppe’s O-Alkyl Carbamate Deprotonation Methodology”
M. J. McGrath and P. O’Brien, Synthesis, 2006, 2233-2241.
77 “Reactivity series for s-BuLi/diamine-mediated lithiation of N-Boc pyrrolidine: applications in catalysis and lithiation of N-Boc piperidine”
M. J. McGrath, J. L. Bilke and P. O’Brien, Chem. Commun., 2006, 2607-2609.
76 “Evaluation of sparteine-like chiral diamines in the enantioselective lithiation-electrophilic trapping of an O-alkyl carbamate”
C. Genet, M. J. McGrath and P. O’Brien, Org. Biomol. Chem., 2006, 4, 1376-1382.
75 “Two-step Synthesis of N-Sulfonyl Aziridines from Epoxides”
J. Huang and P. O’Brien, Synthesis, 2006, 425-434.
74 “Catalytic Asymmetric Deprotonation Using a Ligand Exchange Approach”
M. J. McGrath and P. O’Brien, J. Am. Chem. Soc., 2005, 127, 16378-16379.
73 “Scope and limitations of the catalytic asymmetric rearrangement of epoxides to allylic alcohols using chiral lithium amide bases/lithiated imidazoles”
S. J. Oxenford, J. M. Wright, P. O’Brien, N. Panday and M. R. Shipton, Tetrahedron Lett., 2005, 46, 8315-8318.
72 “Organolithium-mediated conversion of b-functionalised aziridines into alkynyl amino alcohols and diamines”
J. Huang and P. O’Brien, Chem. Commun., 2005, 5696-5698.
71 “Concise Synthesis (±)-Cytisine via Lithiation of N-Boc Bispidine”
D. Stead, P. O’Brien and A. J. Sanderson, Org. Lett., 2005, 7, 4459-4462.
70 “Two-step syntheses of 2,4,6-triisopropylbenzenesulfonyl aziridines”
J. Huang and P. O’Brien, Tetrahedron Lett., 2005, 46, 3253-3256.
69 “Reductive Alkylation of b-Alkoxy Aziridines: New Route to Substituted Allylic Amines”
C. M. Rosser, S. C. Coote, J. P. Kirby, P. O’Brien and D. Caine, Org. Lett., 2004, 6, 4817-4819.
68 “An experimental and computational study of the enantioselective lithiation of N-Boc pyrrolidine using sparteine-like chiral diamines”
P. O’Brien, K. B. Wiberg, W. F. Bailey, J.-P. R. Hermet and M. J. McGrath, J. Am. Chem. Soc., 2004, 126, 15480-15489.
67 “Chiral base route to functionalised cyclopentenyl amines: formal synthesis of the cyclopentene core of nucleoside Q”
S. J. Oxenford, P. O’Brien and M.R. Shipton, Tetrahedron Lett., 2004, 45, 9053-9055.
66 “Crystal structures of (+)-sparteine surrogate adducts of methyllithium and phenyllithium”
C. Strohmann, K. Strohfeldt, D. Schildbach, M. J. McGrath and P. O’Brien, Organometallics, 2004, 23, 5389-5391.
65 “Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis”
M. J. Dearden, M. J. McGrath and P. O’Brien, J. Org. Chem., 2004, 69, 5789-5792.
64 “Concise asymmetric synthesis of (–)-sparteine”
J-P. R. Hermet, M. J. McGrath, P. O’Brien, D. W. Porter and J. Gilday, Chem. Commun., 2004, 1830-1831.
63 “Lithium enolates from a (–)-quinic acid-derived cyclohexanone with a b-alkoxy leaving group: regioselective preparation and evaluation of enolate stability towards b-elimination”
L. M. Murray, P. O’Brien, R. J. K. Taylor and S. Wünnemann, Tetrahedron Lett., 2004, 45, 2596-2601.
62 “cis- and trans-Stereoselective Epoxidation of N-Protected 2-Cyclohexen-1-yl Amines”
P. O’Brien, A. C. Childs, G. J. Ensor, C. L. Hill, J. P. Kirby, M. J. Dearden, S. J. Oxenford and C. M. Rosser, Org. Lett., 2003, 5, 4955-4957.
61 “On the a-lithiation-rearrangement of N-toluenesulfonyl aziridines: mechanistic and synthetic aspects”
P. O’Brien, C. M. Rosser and D. Caine, Tetrahedron, 2003, 59, 9779-9791.
60 “Synthesis of sparteine-like chiral diamines and evaluation in the enantioselective lithiation-substitution of N-(tert-butoxycarbonyl)pyrrolidine”
J-P. R. Hermet, D. W. Porter, M. J. Dearden, J. R. Harrison, T. Koplin, P. O’Brien, J. Parmene, V. Tyurin, A. C. Whitwood, J. Gilday and N. M. Smith, Org. Biomol. Chem., 2003, 1, 3977-3988.
59 “a-Lithiation-rearrangement of N-toluenesulfonyl aziridines with sec-butyllithium and (–)-sparteine: opposite sense of asymmetric induction to epoxides”
P. O’Brien, C. M. Rosser and D. Caine, Tetrahedron Lett., 2003, 44, 6613-6615.
58 “Stereoselective Reactions of a (–)-Quinic Acid-Derived Enone: Application to the Synthesis of the Core of Scyphostatin”
L. M. Murray, P. O’Brien and R. J. K. Taylor, Org. Lett., 2003, 5, 1943-1946.
57 “Chiral lithium amide base-mediated rearrangement of meso-cyclohexene oxides: asymmetric synthesis of amino- and aziridinocyclohexenols”
P. O’Brien and C. D. Pilgram, Org. Biomol. Chem., 2003, 1, 523-534.
56 “An azetidinium ion approach to 3-aryloxy-3-aryl-1-propanamines”
P. O’Brien, D. W. Phillips and T. D. Towers, Tetrahedron Lett., 2002, 43, 7333-7335.
55 “A Readily-Accessible (+)-Sparteine Surrogate”
M. J. Dearden, C. R. Firkin, J-P. R. Hermet and P. O’Brien, J. Am. Chem. Soc., 2002, 124, 11870-11871.
54 “Optimisation of Enantioselectivity for the Chiral Base-mediated Rearrangement of Bis-protected meso-4,5-Dihydroxycyclohexene Oxides: Asymmetric Synthesis of 4-Deoxyconduritols and Conduritol F”
S. E. de Sousa, P. O'Brien and C. D. Pilgram, Tetrahedron, 2002, 58, 4643-4654.
53 “Diastereocontrolled Synthesis of trans- and cis-meso-Cyclopentene Aziridines”
D. Caine, P. O'Brien and C. M. Rosser, Org. Lett., 2002, 4, 1923-1926.
52 “Synthesis and reactions of cyclopentadiene monoaziridine: a concise approach to the core of agelastatin A”
E. Baron, P. O'Brien and T. D. Towers, Tetrahedron Lett., 2002, 43, 723-726.
51 “Diamine Synthesis: Exploring the Regiochemistry of Ring Opening of Aziridinium Ions”
P. O'Brien and T. D. Towers, J. Org. Chem., 2002, 67, 304-307.
50 “Chiral base route to cyclic polyols: asymmetric synthesis of aminodeoxyconduritols and conduritol F”
S. E. de Sousa, P. O'Brien and C. D. Pilgram, Tetrahedron Lett., 2001, 42, 8081-8083.
49 “Asymmetric Synthesis of N-Substituted (R)-2-[(Pyrrolidin-1-yl)methyl]pyrrolidines”
J. R. Harrison and P. O'Brien, Synth. Commun., 2001, 31, 1155-1160.
48 “The synthesis and spectroscopic characterisation of chiral meso-tetraarylmetalloporphyrins bearing meso-pentafluorophenyl groups”
S. P. Foxon, J. R. Lindsay Smith, P. O'Brien and G. Reginato, J. Chem. Soc., Perkin Trans. 2, 2001, 1145-1153.
47 “Evaluation of a sparteine-like diamine for asymmetric synthesis”
J. R. Harrison, P. O'Brien, D. W. Porter and N. M. Smith, Chem. Commun., 2001, 1202-1203.
46 “Practical One-Step Synthesis of Koga's Chiral Bases”
E. Cuthbertson, P. O'Brien and T. D. Towers, Synthesis, 2001, 693-695.
45 “Stoichiometric asymmetric processes”
P. O'Brien, J. Chem. Soc., Perkin Trans. 1, 2001, 95-113.
44 “New route to 4-aminocyclopenten-2-en-1-ols: synthesis and enantioselective rearrangement of 4-amino substituted cyclopentene oxides”
S. Barrett, P. O'Brien, H. C. Steffens, T. D. Towers and M. Voith, Tetrahedron, 2000, 56, 9633-9640.
43 “Asymmetric Synthesis of Cyclic b-Amino Acids”
P. O'Brien, D. W. Porter and N. M. Smith, Synlett, 2000, 1336-1338.
42 “Bispidine-derived N-acyliminium ions in synthesis: stereocontrolled construction of the BCD rings of sparteine”
J. R. Harrison and P. O'Brien, Tetrahedron Lett., 2000, 41, 6167-6170.
41 “Diastereoselective synthesis of sparteine analogues via lithiation-electrophilic quench of N-Boc bispidines”
J. R. Harrison and P. O'Brien, Tetrahedron Lett., 2000, 41, 6161-6165.
40 “Diastereoselective epoxide rearrangements using lithium amide bases: first stereocontrolled synthesis of 4-deoxyconduritols”
A. Kee, P. O'Brien, C. D. Pilgram and S. T. Watson, Chem. Commun., 2000, 1521-1522.
39 “Studies towards the preparation of sparteine-like diamines for asymmetric synthesis”
J. R. Harrison, P. O'Brien, D. W. Porter and N. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1999, 3623-3632.
38 “Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases”
B. Colman, S. E. de Sousa, P. O'Brien, T. D. Towers and W. Watson, Tetrahedron: Asymmetry, 1999, 10, 4175-4182.
37 “Synthesis and Enantioselective Rearrangement of meso-Aziridino Cyclohexene Oxides”
P. O'Brien and C. D. Pilgram, Tetrahedron Lett., 1999, 40, 8427-8430.
36 “A New Norephedrine-derived Chiral Base for Epoxide Rearrangement Reactions”
S. E. de Sousa, P. O'Brien and H. C. Steffens, Tetrahedron Lett., 1999, 40, 8423-8425.
35 “An efficient protocol for a Sharpless-style racemic dihydroxylation”
J. Eames, H. J. Mitchell, A. Nelson, P. O'Brien, S. Warren and P. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1999, 1095-1103.
34 “Chiral base-mediated benzylic functionalisation of (alkyl benzyl ether)tricarbonylchromium(0) complexes: a structure-reactivity study”
S. E. Gibson (née Thomas), P. O'Brien, E. Rahimian and M. H. Smith, J. Chem. Soc., Perkin Trans. 1, 1999, 909-912.
33 “Asymmetric Aminohydroxylation: Scope, Limitations and Use in Synthesis”
P. O'Brien, Angew. Chem., Int. Ed. Engl., 1999, 38, 326-329.
32 “Stereoselective Epoxidation of Cyclic Alkenes Using m-CPBA and Oxone®/Trifluoroacetone – a Comparison”
S. E. de Sousa, P. O'Brien, C. D. Pilgram, D. Roder and T. D. Towers, Tetrahedron Lett., 1999, 40, 391-392.
31 “Unexpected Effect of Protecting Group and Solvent on the Stereoselectivity of m-CPBA Epoxidation of Diprotected cis-4,5-Dihydroxycyclohexenes”
S. E. de Sousa, A. Kee, P. O'Brien and S. T. Watson, Tetrahedron Lett., 1999, 40, 387-390.
30 “Mechanistic and synthetic aspects of stereoselective reactions of lithium derivatives of chiral phosphine oxides: X-ray crystal structure of (1R*,2S*,1'S*,2'R*)-1-(1'-diphenylphosphinoyl-2'-phenylpropyl)-2-phenylsulfanylcyclohexan-1-ol”
C. Guéguen, P. O'Brien, H. R. Powell, P. R. Raithby and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1998, 3405-3417.
29 “Synthesis and Enantioselective Rearrangement of 4-Amino-substituted Cyclopentene Oxides”
P. O'Brien, T. D. Towers and M. Voith, Tetrahedron Lett., 1998, 39, 8175-8178.
28 “Asymmetric aminohydroxylation of substituted styrenes: applications in the synthesis of enantiomerically enriched arylglycinols and a diamine”
P. O'Brien, S. A. Osborne and D. D. Parker, J. Chem. Soc., Perkin Trans. 1, 1998, 2519-2526.
27 “Chiral lithium amide base-mediated rearrangement of diprotected meso 4,5-dihydroxy cyclohexene oxides: enantioselective synthesis of (4R,5S)- and (4S,5R)-4,5-di(tert-butyldimethylsilyloxy)cyclohex-2-enone”
P. O'Brien and P. Poumellec, J. Chem. Soc., Perkin Trans. 1, 1998, 2435-2441.
26 “Two expedient methods for the preparation of chiral diamines”
S. E. de Sousa, P. O'Brien and P. Poumellec, J. Chem. Soc., Perkin Trans. 1, 1998, 1483-1492.
25 “Recent advances in the use of chiral lithium amide bases in synthesis”
P. O'Brien, J. Chem. Soc., Perkin Trans. 1, 1998, 1439-1457.
24 “Asymmetric Aminohydroxylation of Substituted Styrenes Using t-Butyl Carbamate”
P. O'Brien, S. A. Osborne and D. D. Parker, Tetrahedron Lett., 1998, 39, 4099-4102.
23 “Stereocontrolled Synthesis of Functionalised Cyclohexanes via the Lithium Amide-mediated Rearrangement of a meso-4,5-Disubstituted Cyclohexene Oxide”
P. O'Brien and J. J. Tournayre, Tetrahedron, 1997, 53, 17527-17542.
22 “Two Step Synthesis of C2 Symmetric 2,3-Diarylalkyloxybenzaldehydes – A Mitsunobu Approach”
J. R. Lindsay Smith, P. O'Brien and G. Reginato, Tetrahedron: Asymmetry, 1997, 8, 3415-3420.
21 “Two useful methods for the preparation of (R)- and (S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)ethanamine”
S. E. de Sousa, P. O'Brien and P. Poumellec, Tetrahedron: Asymmetry, 1997, 8, 2613-2618.
20 “Aziridinium Ions from Phenylglycinol – A New Approach to the Synthesis of Chiral Diamines”
S. E. de Sousa and P. O'Brien, Tetrahedron Lett., 1997, 38, 4885-4888.
19 “Cyclobutanone as an electrophile for lithiated phosphine oxides: “Internal Quench” Conditions”
C. Guéguen, P. O'Brien, S. Warren and P. Wyatt, J. Organomet. Chem., 1997, 529, 279-283.
18 “Experimental and Molecular Orbital Calculational Study of the Stereoselective Horner-Wittig Reaction with Phosphine Oxides: Control of Stereoselectivity by Lithium”
D. R. Armstrong, D. Barr, M. G. Davidson, G. Hutton, P. O'Brien, R. Snaith and S. Warren, J. Organomet. Chem., 1997, 529, 29-33.
17 “Investigation of the configurational stability of lithiated phosphine oxides using the Hoffmann test: X-ray structures of (2R*,3S*,4S*)-4-(N,N-dibenzylamino)-2-diphenylphosphinoyl-5-phenylpentan-3-ol and (2S*,4S*)-4-(N,N-dibenzylamino)-2-diphenylphosphinoyl-5-phenylpentan-3-one”
P. O'Brien, H. R. Powell, P. R. Raithby and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1997, 1031-1039.
16 “Asymmetric Synthesis with Diphenylphosphine Oxides: Bicyclic Aminals and Oxazolidines as Chiral Auxiliaries”
P. O'Brien and S. Warren, Tetrahedron: Asymmetry, 1996, 7, 3431-3444.
15 “Investigation of the configurational stability of lithiated phosphine oxides using diastereomerically pure and enantiomerically enriched phosphine oxides”
P. O'Brien and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1996, 2567-2573.
14 “Chiral Base-mediated Rearrangement of meso-Cyclohexene Oxides to Allylic Alcohols”
P. O'Brien and P. Poumellec, Tetrahedron Lett., 1996, 37, 8057-8058.
13 “Chiral Phosphine Oxides and Chiral Esters in Stereoselective Intermolecular Acylation Reactions of Phosphine Oxides”
D. Cavalla, C. Guéguen, A. Nelson, P. O'Brien, M. G. Russell and S. Warren, Tetrahedron Lett., 1996, 37, 7465-7468.
12 “Highly Stereoselective Hydroxy-alkylation, Silylation and Alkylation Reactions of Lithium Derivatives of Chiral Phosphine Oxides”
C. Guéguen, H. J. Mitchell, P. O'Brien and S. Warren, Tetrahedron Lett., 1996, 37, 7461-7464.
11 “Amino Acid Derived Thiane Oxide and Dioxide Systems as Disposable Templates: Synthesis of a-Amino Ketones, anti amino alcohols and an Amino Cyclopentenone”
M. P. Gamble, G. M. P. Giblin, J. G. Montana, P. O'Brien, T. P. Ockenden and R. J. K. Taylor, Tetrahedron Lett., 1996, 37, 7457-7460.
10 “Synthesis of R or S diphenylphosphinoyl hydroxy aldehydes and 1,2 diols using Mukaiyama's bicyclic aminal methodology and Sharpless asymmetric dihydroxylation”
P. O'Brien and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1996, 2129-2138.
9 “Stereocontrolled route to some optically active b-hydroxy phosphine oxides using the stereoselective addition of metallated phosphine oxides to proline-derived keto aminals”
P. O'Brien and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1996, 2117-2127.
8 “A Simple and Efficient Method for the Preparation of Homochiral Amines: Application to the Synthesis of a New C2 Symmetric Triamine”
P. O'Brien and P. Poumellec, Tetrahedron Lett., 1996, 37, 5619-5622.
7 “Cesium Fluoride-mediated Horner-Wittig Addition Reactions of Silyl Phosphine Oxides; Synthesis of Optically Active Silyl Phosphine Oxides Using Chiral Bases and a Chiral Acid”
P. O'Brien and S. Warren, Synlett, 1996, 579-581.
6 “Synthesis of Phenylalanine-derived b-Hydroxy and b-Keto Phosphine Oxides – Investigation of the Configurational Stability of Lithiated Phosphine Oxides Using the Hoffmann Test”
P. O'Brien and S. Warren, Tetrahedron Lett., 1996, 37, 4271-4274.
5 “Norephedrine-derived Oxazolidines as Chiral Auxiliaries – Stereocontrolled Routes to R or S b-Hydroxy Phosphine Oxides”
P. O'Brien and S. Warren, Tetrahedron Lett., 1996, 37, 3051-3054.
4 “On the Configurational Stability of Lithiated Phosphine Oxides”
P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 8473-8476.
3 “Asymmetric Dihydroxylations of Allylic Phosphine Oxides”
A. Nelson, P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2685-2688.
2 “Stereocontrolled Synthesis of R or S Diphenylphosphinoyl Hydroxy Aldehydes and 1,2 Diols Using Bicyclic Aminals”
P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2681-2684.
1 “An Efficient Protocol for a Sharpless Style Racemic Dihydroxylation”
J. Eames, H. J. Mitchell, A. Nelson, P. O'Brien, S. Warren and P. Wyatt, Tetrahedron Lett., 1995, 36, 1719-1722.
Kevin was born and raised in Berlin, Germany, where he also conducted his undergraduate studies at the Humboldt Universität zu Berlin. Research projects included the synthesis of Tamoxifen derivatives (Oliver Seitz) and the elucidation of structures and dynamics of photoswitchable Grubbs-type catalysts (Clemens Mügge, Stefan Hecht). Kevin then moved to the University of St Andrews, Scotland, to pursue a PhD in organocatalysis under the supervision of Andrew D. Smith. Studies included the NHC-catalysed Steglich rearrangement of pyrazolyl carbonates, the quinidine-catalysed formal [4+2] cycloaddition of ethyl 2,3-butadienoate to CF3-enones and the isothiourea-catalysedr earrangement of quaternary ammonium salts. Kevin currently investigates the racemic and enantioselective α-lithiation and trapping of saturated heterocycles within the POB group.
Will carried out his MChem degree at the University of York. He spent his final year under the supervision of Professor Richard Taylor and Dr. Timothy Hurst to explore synthesis of a range of carbonyl-linked bisoxindole structures. He is currently working towards a PhD in the O’Brien and Duckett groups on a range of isotopically-labelled nicotines and related structures with a view towards medicinal imaging applications such as MRI. This involves their synthesis, subsequent hyperpolarisation by Signal Enhancement By Reversible Exchange (SABRE) and evaluation/optimisation of their magnetic properties. His project is sponsored by the EPSRC and Bruker.
Tom studied for his undergraduate degree at Oxford University, where he spent his masters year working on the synthesis of novel antibiotics based on a tetramate core. He now works as a PhD student in the O'Brien group on the 3D fragment project, continuing to synthesise interesting molecules for drug discovery. Outside of the lab, Tom enjoys rugby, cricket and corralling the rest of the group into board game nights.
Paul did his Mchem at the University of the Nottingham, with an integrated year in industry at Sygnature discovery. His masters project was funded by GSK, focusing on idiopathic pulmonary fibrosis. He is currently working towards a PhD on the design and synthesis of 3-D fragments to explore new areas of pharmaceutical space in collaboration with Astex, Astra Zeneca, Ely Lilly, Pfizer and Vernalis.
Hanna completed her MSc research on the Synthesis of Antimalarial Antifolates at the University of the Witwatersrand, South Africa. At the end of 2013, she moved to the US and began working for Endocyte Inc., an American biopharmaceutical company situated within Purdue University’s Research Park. Here, she worked on the development of Small Molecule Drug Conjugates (SMDCs) as part of a targeted therapy approach for the treatment of cancer and inflammatory diseases. She joined the O'Brien group in 2016 as part of the EU funded, Marie Curie Actions, Innovative Training Network (ITN), FragNet where she is currently working on her PhD studies on the Design and Synthesis of Novel 3D Lead-Like Compounds.
Sophie graduated from the University of Leeds (MChem) with a placement involving research of an opioid addiction treatment drug and its impurities, in order for the drug to be approved. Sophie is currently working towards a PhD in the O’Brien, Parkin and Chechik groups. Her research involves the late-stage functionalisation of drug-like scaffolds by electrochemically-generated free radicals.
Lewis carried out his BSc degree at the University of Salford also completing a placement year at KidScan cancer research charity. The research involved developing an improved organolithium methodology for an asymmetric synthesis of diarylmethane derivatives under Dr. Jim Wilkinson. In his final year he worked on an independent research project utilising organolithium approaches towards the synthesis of dehydroemetine analogues for use as an anti-malarial agent. He is currently working towards a PhD in the Fascione and O’Brien groups establishing novel approaches for the bio-orthogonal modification of proteins. His project is sponsored by the EPSRC. When not at his fume hood, Lewis can be found playing his guitar, listening to music and tweeting excessively (@LewisMGooch).
Nico carried out his BSc and MSc Chemistry at RWTH Aachen in Germany, graduating in 2016. He spent the last six months for his MSc dissertation at the University of York in the O'Brien group examining novel organolithium methodology. After a short intership at the Université de Rouen in France he decided to return to the O'Brien group in January 2017 working towards a PhD and is investigating C-H functionalisation of heterocycles using organolithium reagents.
Giordaina completed her undergraduate degree at Teesside University, with an industrial placement year at the pharmaceutical company Covance. She completed her MSc by research at the University of York as part of the O’Brien group and has stayed on to undertake a PhD. Her research focuses on the C-H functionalisation of sulfoximines using organolithium reagents. In her spare time, Giordaina enjoys ice skating, drawing, baking and bribing her colleagues with cake.
Matthew completed his undergraduate degree (MChem) at York, spending the final year on placement with AstraZeneca in Cambridge as a synthetic chemist. During this placement he also investigated oxidative cleavage using lutidine as an additive. He then returned to York to join the O’Brien group working toward a PhD investigating the lithiation of nitrogen heterocycles. Beyond chemistry Matthew enjoys games of all descriptions, particularly card games.
Alex carried out her BSc at Keele University, focusing on the synthesis of novel antimalarial agents for her final year project. She additionally undertook a year in industry at the pharmaceutical company AstraZeneca, where her research contributed to the approval of a new blood cancer drug. Alex is now studying her MSc by research in the O'Brien group at the University of York. Her research focuses on the C-H functionalisation of sulfoximines using organolithium reagents.
Andres Gomez Angel