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Oxidative Umpolung α-Alkylation of Ketones

O. Svetlana Shneider, Evgeni Pisarevsky, Peter Fristrup and Alex M. Szpilman*

*Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, 3200008, Haifa, Israel, Email: Szpilmantx.technion.ac.il

O. S. Shneider, E. Pisarevsky, P. Fristrup, A. M. Szpilman, Org. Lett., 2015, 17, 282-285.

DOI: 10.1021/ol503384c (free Supporting Information)


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Abstract

A hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source is applicable to a broad range of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in very good yield. Meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies suggest an ionic mechanism.

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Key Words

alkylation, hypervalent iodine compounds


ID: J54-Y2015