Document Type

Article

Publication Title

ARKIVOC

Department

Chemistry

ISSN

1551-7012

Volume

2015

Issue

7

DOI

10.3998/ark.5550190.p009.321

First Page

172

Last Page

194

Publication Date

1-1-2015

Abstract

Numerous methods for the stereoselective synthesis of chiral compounds exist in the literature, which use chiral templates or catalysts. Only in a limited number of cases have achiral catalysts been shown to significantly influence the stereochemical outcomes of reactions. Previous studies in our laboratories have revealed the achiral acyl-transfer catalyst pyridine to alter the stereochemical outcome of the reaction of racemic trans-2-substituted cyclohexanols with racemic 2-chloropropionyl chloride and cause a reversal of diastereoselectivity. The current paper presents the application of the reaction scheme to a wider number of substrates and reveals the importance of the heteroatom in the trans-2-substituent

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