The conformational bias of aryl, arylsulfonyl geminally substituted tertiary carbon centers: applications in substrate-based stereocontrol |
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| Authors: | Scott Jeremy P Mullens Peter R Brewer Sarah E Brands Karel M J Chilenski Jennifer R Davies Antony J Gibb Andrew D Lieberman David R Oliver Steven F Dolling Ulf-H |
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| Institution: | Department of Process Research, Merck Sharp & Dohme Research Laboratories, Hoddesdon, Hertfordshire, UK. jeremy_scott@merck.com |
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| Abstract: | Intramolecular nitrile oxide-olefin cycloaddition to form hexahydrobenzisoxazole 14, which engenders a phenylsulfonyl, 2,5-difluorophenyl geminally substituted carbon substructure, proceeds with up to 99% ds. A rationalization of the high level of substrate-based stereo-induction observed in this and related ketone and acrylonitrile metallohydride reductions, supported by single crystal X-ray crystallography, is presented. |
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