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Issue 6, 2013
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Copper-dipyridylphosphine-catalyzed hydrosilylation: enantioselective synthesis of aryl- and heteroarylcycloalkyl alcohols

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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

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Publication details

The article was received on 18 Oct 2012, accepted on 29 Nov 2012 and first published on 29 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB27040D
Org. Biomol. Chem., 2013,11, 929-937

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    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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