Silicon‐Directed Nazarov Reactions II. Preparation and Cyclization of β‐Silyl‐substituted Divinyl Ketones

Todd K. Jones, Scott E. Denmark

Research output: Contribution to journalArticlepeer-review

Abstract

Two general methods for the preparation of β‐silyl‐substituted divinyl ketones have been developed starting from either α, β‐unsaturated aldehydes or simple ketones. Anhydrous FeCl3 induces the cyclization to cyclopentenones under mild conditions and in good yields with predictable and complete control over the position of the double bond in the five‐membered ring. The observed effects of substituents on rate can be explained by a rate‐determining cationic electrocyclization. Silyl substitution has been shown to retard the reaction.

Original languageEnglish (US)
Pages (from-to)2377-2396
Number of pages20
JournalHelvetica Chimica Acta
Volume66
Issue number8
DOIs
StatePublished - Jan 1 1983

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Silicon‐Directed Nazarov Reactions II. Preparation and Cyclization of β‐Silyl‐substituted Divinyl Ketones'. Together they form a unique fingerprint.

Cite this