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Issue 9, 2015
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Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles

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Abstract

Umpolung alkylation of Evans’ auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3 : 1 and 18 : 1. Dialkylzinc serves as the nucleophile and umpolung of the β-keto-imide enolate is achieved by the action of Koser's reagent.

Graphical abstract: Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles

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Article information


Submitted
13 Dec 2014
Accepted
06 Jan 2015
First published
06 Jan 2015

Org. Biomol. Chem., 2015,13, 2546-2549
Article type
Communication

Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles

T. A. Targel, J. N. Kumar, O. S. Shneider, S. Bar, N. Fridman, S. Maximenko and A. M. Szpilman, Org. Biomol. Chem., 2015, 13, 2546
DOI: 10.1039/C4OB02601B

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