研究领域

Development and use of new methods in asymmetric synthesis

The O’Brien group’s research focuses on contemporary organic synthesis, with a particular interest in asymmetric synthesis, namely the synthesis of single enantiomers of chiral molecules. All of the projects in the group aim to develop selective and synthetically useful methods that are technically simple, high yielding and robust. Current research projects are focused in three distinct areas: Organolithium Methodology for the Synthesis of Nitrogen Heterocycles Design, Synthesis and Biological Screening of 3-D Fragments Synthetic Tools for Chemical Biology

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Synthesis of Enantiopure Piperazines via Asymmetric Lithiation-Trapping of N-Boc Piperazines: Unexpected Role of the Electrophile and Distal N-Substituent J Am Chem Soc, 2016, 138, 651. Mechanistic Interrogation of the Asymmetric Lithiation-trapping of N-Thiopivaloyl Azetidine and Pyrrolidine Chem Commun, 2016, 52, 1354. Silver(I) or copper(II)-mediated dearomatisation of aromatic ynones: direct access to spirocyclic scaffolds Angew Chem Int Ed, 2015, 54, 7640. Lead-oriented synthesis: investigation of organolithium-mediated routes to 3-D scaffolds and 3-D shape analysis of a virtual lead-like library Bioorg Med Chem, 2015, 23, 2680. Revisiting the sparteine surrogate: development of a resolution route to the (–)-sparteine surrogate Org Biomol Chem, 2014, 12, 9357. Asymmetric Lithiation-Trapping of N-Boc Heterocycles at Temperatures above –78 °C Org Lett, 2013, 15, 5424. Preparation and Reactions of Enantiomerically Pure a-Functionalised Grignard Reagents J Am Chem Soc, 2013, 135, 8071. Stereocontrolled Synthesis of the AB Rings of Samaderine C Org Lett, 2013, 15, 394. 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 J Am Chem Soc, 2012, 134, 5300. Enantioselective, Palladium-Catalyzed a-Arylation of N-Boc Pyrrolidine: In Situ React IR Spectroscopic Monitoring, Scope and Synthetic Applications J Org Chem, 2011, 76, 5936.