Silicon-directed Nazarov cyclizations. 8. Stereoelectronic control of torquoselectivity

Scott E Denmark, Michael A. Wallace, Christopher B. Walker

Research output: Contribution to journalArticle

Abstract

The silicon-directed Nazarov cyclization of the optically active β′-silyldivinyl ketones (+)-1 and (-)-1 proceeded with near perfect stereoselectivity. The direction of conrotatory electrocyclic ring closure was controlled by the remote silyl group such that carbon-carbon bond formation occurred in an anti SE′ sense to the silicon electrofuge.

Original languageEnglish (US)
Pages (from-to)5543-5545
Number of pages3
JournalJournal of Organic Chemistry
Volume55
Issue number21
StatePublished - Dec 1 1990

ASJC Scopus subject areas

  • Organic Chemistry

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