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
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.
Comments
Click here to view the Conference Organization's website
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/