Issue 6, 2013

Copper-dipyridylphosphine-catalyzed hydrosilylation: enantioselective synthesis of aryl- and heteroarylcycloalkyl alcohols

Abstract

The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the steric size of cycloalkyl groups has a significant influence on the reaction outcomes. The first stereoselective formation of a selection of cyclohexyl heteroaryl alcohols of up to 97% enantiopurity was realized as well. Dramatic temperature effects on both the enantiopurity and the absolute configuration of the alcohol products were observed in the reduction of some cyclohexyl pyridyl ketones.

Graphical abstract: Copper-dipyridylphosphine-catalyzed hydrosilylation: enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols

Supplementary files

Article information

Article type
Paper
Submitted
18 Oct 2012
Accepted
29 Nov 2012
First published
29 Nov 2012

Org. Biomol. Chem., 2013,11, 929-937

Copper-dipyridylphosphine-catalyzed hydrosilylation: enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols

S. Qi, M. Li, S. Li, J. Zhou, J. Wu, F. Yu, X. Zhang, A. S. C. Chan and J. Wu, Org. Biomol. Chem., 2013, 11, 929 DOI: 10.1039/C2OB27040D

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