Phosphonamide Stabilized Allylic Carbanions. New Homoenolate Anion Equivalents

David A. Evans; James M. Takacs; Kenneth M. Hurst

doi:10.1021/ja00496a016

Phosphonamide Stabilized Allylic Carbanions. New Homoenolate Anion Equivalents

David A. Evans, James M. Takacs, Kenneth M. Hurst

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

113 Scopus citations

Abstract

The chemistry of phosphonamide stabilized allylic carbanions derived from the 1,2-addition of tervalent phosphorus siloxanes with α,β-unsaturated aldehydes has been studied. An in situ synthesis of allylic α-silyloxyphosphonamides, followed by metalation and regioselective γ-alkylation of the allylic carbanion, yields a versatile “active ester”. Transesterification under mild conditions gives esters and lactones and defines a new homoenolate equivalency.

Original language	English (US)
Pages (from-to)	371-378
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	101
Issue number	2
DOIs	https://doi.org/10.1021/ja00496a016
State	Published - Feb 1 1979
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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AU - Takacs, James M.

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AB - The chemistry of phosphonamide stabilized allylic carbanions derived from the 1,2-addition of tervalent phosphorus siloxanes with α,β-unsaturated aldehydes has been studied. An in situ synthesis of allylic α-silyloxyphosphonamides, followed by metalation and regioselective γ-alkylation of the allylic carbanion, yields a versatile “active ester”. Transesterification under mild conditions gives esters and lactones and defines a new homoenolate equivalency.

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Phosphonamide Stabilized Allylic Carbanions. New Homoenolate Anion Equivalents

Abstract

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