Acylation of trans-2-substituted cyclohexanols: The impact of substituent variation on the pyridine-induced reversal of diastereoselectivity

Authors

Sven Hackbusch, University of the PacificFollow
Andreas H. Franz, University of the PacificFollow

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

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Recommended Citation

Hackbusch, S., & Franz, A. H. (2015). Acylation of trans-2-substituted cyclohexanols: The impact of substituent variation on the pyridine-induced reversal of diastereoselectivity. ARKIVOC, 2015(7), 172–194. DOI: 10.3998/ark.5550190.p009.321
https://scholarlycommons.pacific.edu/cop-facarticles/160