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Issue 10, 2012

Copper(i) catalyzed asymmetric 1,2-addition of Grignard reagents to α-methyl substituted α,β-unsaturated ketones

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Abstract

The first catalytic enantioselective 1,2-addition of Grignard reagents to ketones is presented. This additive-free copper(I) catalyzed 1,2-addition provides chiral allylic tertiary alcohols with an er of up to 98 : 2 and excellent yields due to the complete shift of overwhelming 1,4-selectivity of copper(I)-catalysts towards 1,2-selectivity in the addition reaction to enones.

Graphical abstract: Copper(i) catalyzed asymmetric 1,2-addition of Grignard reagents to α-methyl substituted α,β-unsaturated ketones

Supplementary files

Article information


Submitted
30 Oct 2011
Accepted
16 Nov 2011
First published
16 Nov 2011

Chem. Commun., 2012,48, 1478-1480
Article type
Communication

Copper(I) catalyzed asymmetric 1,2-addition of Grignard reagents to α-methyl substituted α,β-unsaturated ketones

A. V. R. Madduri, A. J. Minnaard and S. R. Harutyunyan, Chem. Commun., 2012, 48, 1478 DOI: 10.1039/C1CC16725A

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