Oxidative umpolung α-alkylation of ketones

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.

Original languageEnglish
Pages (from-to)282-285
Number of pages4
JournalOrganic Letters
Issue number2
StatePublished - 16 Jan 2015
Externally publishedYes


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