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Presentation
Acylation of trans-2-substituted cyclohexanols: Reversal of diastereoselectivity depends on scaffold substitution and achiral amine catalyst
248th American Chemical Society (ACS) National Meeting
  • Sven Hackbusch, University of the Pacific
  • Amelia Watson
  • Andreas H. Franz, University of the Pacific
Document Type
Conference Presentation
Department
Chemistry
Organization
American Chemical Society (ACS)
Location
San Francisco, CA
Conference Dates
August 10-14, 2014
Date of Presentation
8-10-2014
Disciplines
Abstract
We report progress in the investigation of previously observed amine-induced changes in diastereoselectivity during acylations of several chiral templates. The presence of simple achiral amines during acylation of racemic trans-1,2-substituted cyclohexanols with racemic 2-chloro-propionyl chloride affected the diastereomeric ratio (dr) of the products. The linear load-dependence on the dr in the case of pyridine and DMAP led to reversal of diastereoselectivity overall. The reaction kinetics were investigated by NMR spectroscopy, and computational results supporting a proposed mechanism are presented.
Citation Information
Sven Hackbusch, Amelia Watson and Andreas H. Franz. "Acylation of trans-2-substituted cyclohexanols: Reversal of diastereoselectivity depends on scaffold substitution and achiral amine catalyst" 248th American Chemical Society (ACS) National Meeting (2014)
Available at: http://works.bepress.com/andreas-franz/93/