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Issue 14, 2012
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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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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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Publication details

The article was received on 11 Jan 2011, accepted on 30 Jan 2012 and first published on 05 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25080B
Citation: Org. Biomol. Chem., 2012,10, 2878-2884
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    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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