Reactions of silylmethyl allylic silanes: Synthesis of tetrahydrofurans

Jacqueline H. Smitrovich, K. A. Woerpel

Research output: Contribution to journalReview article

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
DOIs
StatePublished - 2002

Keywords

  • Annulation reaction
  • Rearangements
  • Silylmethyl allylic silanes
  • Tetrahydrofurans

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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