Silicon‐Directed Nazarov Cyclizations. Part V. Substituent and heteroatom effects on the reaction

Scott E. Denmark, Karl L. Habermas, Gary A. Hite

Research output: Contribution to journalArticle

Abstract

The ability to incorporate alkyl, alkenyl, aryl, and heteroatomic groups into substrates for the silicon‐directed Nazarov cyclization and their subsequent reactions has been investigated. In general, most of the groups are compatible with the conditions for the cyclization and do not interfere even when directly attached to the divinyl ketone. The influence of substituents on the rate of the cyclization has been addressed and is consistent with a simple mechanistic picture. O‐ and N‐Containing functions are tolerated except when attached to the α‐vinyl C‐atom of the divinyl ketone. The diastereoface‐directing effect of a fused cyclobutane is discussed.

Original languageEnglish (US)
Pages (from-to)168-194
Number of pages27
JournalHelvetica Chimica Acta
Volume71
Issue number1
DOIs
StatePublished - Feb 3 1988

ASJC Scopus subject areas

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

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