The first example of amine-induced reversal of diastereoselectivity in acylation of some trans-2-substituted cyclohexanols

Authors

Andrey V. Samoshin, University of the Pacific
Jasper Visser
Matthew CurtisFollow
Vyacheslav V. Samoshin, University of the PacificFollow
Andreas H. Franz, University of the PacificFollow

Document Type

Article

Publication Title

ARKIVOC

Department

Chemistry

ISSN

1551-7012

Volume

2012

Issue

8

DOI

10.3998/ark.5550190.0013.803

First Page

27

Last Page

35

Publication Date

1-1-2012

Abstract

The reaction between racemic acyl chlorides and racemic trans-2-substituted-cyclohexanols proceeds diastereoselectively. We found for the first time that addition of a tertiary amine not only accelerates the acylation, but for some substituents leads to complete inversion of diastereoselectivity. These observations have been rationalized in terms of a possible stereoselective intramolecular assistance by the substituent group during the acylation of the neighboring hydroxyl group.

Creative Commons License

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

Recommended Citation

Samoshin, A. V., Visser, J., Curtis, M., Samoshin, V. V., & Franz, A. H. (2012). The first example of amine-induced reversal of diastereoselectivity in acylation of some trans-2-substituted cyclohexanols. ARKIVOC, 2012(8), 27–35. DOI: 10.3998/ark.5550190.0013.803
https://scholarlycommons.pacific.edu/cop-facarticles/129