Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

David M. Guptill; Carolyn M. Cohen; Huw M.L. Davies

doi:10.1021/ol4028978

Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

David M. Guptill, Carolyn M. Cohen, Huw M.L. Davies

Chemistry (Twin Cities)

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

15 Scopus citations

Abstract

The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.

Original language	English (US)
Pages (from-to)	6120-6123
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	24
DOIs	https://doi.org/10.1021/ol4028978
State	Published - Dec 20 2013

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title = "Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes",

abstract = "The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.",

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AB - The rhodium-catalyzed decomposition of 2-(triisopropylsilyl)ethyl aryl- and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C-H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.

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Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes

Abstract

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