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Articles by Iain Coldham
Synthesis of Enantioenriched Spirocyclic 2-Arylpiperidines via Kinetic Resolution
Synthesis of Enantioenriched Spirocyclic 2-Arylpiperidines via Kinetic Resolution Kinetic resolution of N-Boc-spirocyclic 2-arylpiperidines with spiro substitution at C-4 was achieved with high enantiomeric ratios using the chiral base n-BuLi/sparteine. Cyclopropanation or metallaphotoredox catalysis were used to access the piperidines, which could be further functionalised without loss of enantiopurity, highlighting their use as potential 3D fragments for drug discovery.
Synthesis and Kinetic Resolution of Substituted Tetrahydroquinolines by Lithiation then Electrophilic Quench
Treatment of N-Boc-2-aryl-1,2,3,4-tetrahydroquinolines with n-butyllithium in THF at –78 °C resulted in efficient lithiation at the 2-position and the organolithiums were trapped with a variety of electrophiles to give substituted products. Variable temperature NMR spectroscopy gave kinetic data that showed that the rate of tert-butoxycarbonyl (Boc) rotation was fast (?G‡ ? 45 kJ/mol at –78 °C) and in situ ReactIR spectroscopy showed fast lithiation at –78 °C.
Synthesis and kinetic resolution of substituted tetrahydroquinolines by lithiation then electrophilic quench
Treatment of N-Boc-2-aryl-1,2,3,4-tetrahydroquinolines with n-butyllithium in THF at ?78 °C resulted in efficient lithiation at the 2-position and the organolithiums were trapped with a variety of electrophiles to give substituted products. Variable temperature NMR spectroscopy gave kinetic data that showed that the rate of tert-butoxycarbonyl (Boc) rotation was fast (?G ? 45 kJ mol at ?78 °C) and in situ ReactIR spectroscopy showed fast lithiation at ?78 °C.
Highly enantioselective metallation-substitution alpha to a chiral nitrile
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