Reactions of silylmethyl allylic silanes: Synthesis of tetrahydrofurans

Jacqueline H. Smitrovich, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Allylic silanes bearing a silylmethyl group at the allylic position were prepared as both (E)- and (Z)-alkene stereoisomers. These compounds undergo reactions with aldehydes in the presence of Lewis acids to provide tetrahydrofurans, bearing up to five stereogenic centers, as single diastereomers. These annulation processes are likely facilitated because the reactions proceed via carbocations that are stabilized by two β-silyl substituents.

Original languageEnglish (US)
Pages (from-to)2778-2785
Number of pages8
JournalSynthesis
Issue number18
StatePublished - 2002

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Bearings (structural)
Furans
Silanes
Lewis Acids
Stereoisomerism
Alkenes
Aldehydes
Olefins
Acids

Keywords

  • Annulation reaction
  • Rearangements
  • Silylmethyl allylic silanes
  • Tetrahydrofurans

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Reactions of silylmethyl allylic silanes : Synthesis of tetrahydrofurans. / Smitrovich, Jacqueline H.; Woerpel, Keith.

In: Synthesis, No. 18, 2002, p. 2778-2785.

Research output: Contribution to journalArticle

Smitrovich, Jacqueline H. ; Woerpel, Keith. / Reactions of silylmethyl allylic silanes : Synthesis of tetrahydrofurans. In: Synthesis. 2002 ; No. 18. pp. 2778-2785.
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