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

Scott E. Denmark, David C. Forbes

Research output: Contribution to journalArticle

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 A1,2 strain from the β-methyl group.

Original languageEnglish (US)
Pages (from-to)5037-5040
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number35
DOIs
StatePublished - Aug 25 1992

Fingerprint

Hydrosilylation
Lactones
Silicon
Esters

Keywords

  • A strain
  • Platinum-catalyzed, intramolecular hydrosilylation
  • diastereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A stereochemical study on the intramolecular hydrosilylation of α,β-unsaturated esters. / Denmark, Scott E.; Forbes, David C.

In: Tetrahedron Letters, Vol. 33, No. 35, 25.08.1992, p. 5037-5040.

Research output: Contribution to journalArticle

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