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Issue 14, 2012
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Access to chiral α-bromo and α-H-substituted tertiary allylic alcoholsvia copper(i) catalyzed 1,2-addition of Grignard reagents to enones

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Abstract

The catalytic asymmetric synthesis of tertiary alcohols by the addition of organometallic reagents to ketones is of central importance in organic chemistry. The resulting quaternary stereocentres are difficult to prepare selectively by other means despite their widespread occurrence in natural products and pharmaceuticals. Here we report on a new methodology which allows access to both α-bromo-substituted and α-H-substituted allylic tertiary alcohols with excellent yields, and enantioselectivities of up to 98% using the copper(I)-catalysed 1,2-addition of Grignard reagents to enones. As an example, the methodology is applied in the synthesis of a chiral dihydrofuran.

Graphical abstract: Access to chiral α-bromo and α-H-substituted tertiary allylic alcohols via copper(i) catalyzed 1,2-addition of Grignard reagents to enones

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Submitted
11 Jan 2011
Accepted
30 Jan 2012
First published
05 Mar 2012

Org. Biomol. Chem., 2012,10, 2878-2884
Article type
Paper

Access to chiral α-bromo and α-H-substituted tertiary allylic alcohols via copper(I) catalyzed 1,2-addition of Grignard reagents to enones

A. V. R. Madduri, A. J. Minnaard and S. R. Harutyunyan, Org. Biomol. Chem., 2012, 10, 2878
DOI: 10.1039/C2OB25080B

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