Oxidative umpolung α-alkylation of ketones

O. Svetlana Shneider; Evgeni Pisarevsky; Peter Fristrup; Alex M. Szpilman

doi:10.1021/ol503384c

Oxidative umpolung α-alkylation of ketones

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

Research output: Contribution to journal › Article › peer-review

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Abstract

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 language	English
Pages (from-to)	282-285
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	2
DOIs	https://doi.org/10.1021/ol503384c
State	Published - 16 Jan 2015
Externally published	Yes

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abstract = "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.",

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AU - Shneider, O. Svetlana

AU - Pisarevsky, Evgeni

AU - Fristrup, Peter

AU - Szpilman, Alex M.

PY - 2015/1/16

Y1 - 2015/1/16

N2 - 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.

AB - 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.

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Oxidative umpolung α-alkylation of ketones

Abstract

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