A stereochemical study on the intramolecular hydrosilylation of α,β-unsaturated esters

Scott E. Denmark; David C. Forbes

doi:10.1016/S0040-4039(00)61182-6

A stereochemical study on the intramolecular hydrosilylation of α,β-unsaturated esters

Scott E. Denmark, David C. Forbes

Chemistry

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

Abstract

The intramolecular hydrosilylation of several 3-methyl-4-siloxy-2-butenoates afforded cis disubstituted lactones after desilylation. The diastereoinduction was sensitive to the bulk of the allylic substituent, but not to the groups on silicon. The origin of asymmetric induction is believed to be the A^1,2 strain from the β-methyl group.

Original language	English (US)
Pages (from-to)	5037-5040
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(00)61182-6
State	Published - Aug 25 1992

Keywords

A strain
Platinum-catalyzed, intramolecular hydrosilylation
diastereoselectivity

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)61182-6

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AU - Forbes, David C.

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AB - The intramolecular hydrosilylation of several 3-methyl-4-siloxy-2-butenoates afforded cis disubstituted lactones after desilylation. The diastereoinduction was sensitive to the bulk of the allylic substituent, but not to the groups on silicon. The origin of asymmetric induction is believed to be the A1,2 strain from the β-methyl group.

KW - A strain

KW - Platinum-catalyzed, intramolecular hydrosilylation

KW - diastereoselectivity

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A stereochemical study on the intramolecular hydrosilylation of α,β-unsaturated esters

Abstract

Keywords

ASJC Scopus subject areas

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