Title

Acylation of trans-2-substituted cyclohexanols: Reversal of diastereoselectivity depends on scaffold substitution and achiral amine catalyst

Document Type

Conference Presentation

Department

Chemistry

Conference Title

248th American Chemical Society (ACS) National Meeting

Organization

American Chemical Society (ACS)

Location

San Francisco, CA

Conference Dates

August 10-14, 2014

Date of Presentation

8-10-2014

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.

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