Issue 10, 2012
From the journal:

Chemical Communications

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

Ashoka V. R. Madduri,a   Adriaan J. Minnaard*a  and  Syuzanna R. Harutyunyan*a  

* Corresponding authors

a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, Groningen, The Netherlands
E-mail: s.harutyunyan@rug.nl, a.j.minnaard@rug.nl
Fax: +31-50-363-4296
Tel: +31-50-363-3539

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

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Article information

DOI
https://doi.org/10.1039/C1CC16725A
Article type
Communication
Submitted
30 Oct 2011
Accepted
16 Nov 2011
First published
16 Nov 2011

Chem. Commun., 2012,48, 1478-1480

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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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