Silicon-directed nazarov cyclizations-IV. Further studies in stereochemical control

Scott E. Denmark, Karl L. Habermas, Gary A. Hite, Todd K. Jones

Research output: Contribution to journalArticle

Abstract

The silicon-directed Nazarov cyclization was shown to proceed with good to excellent stereoselectivity in cyclohexenyl systems bearing a variety of ring substituents. In all cases the trans family of isomers predominated, and cis ring-fused products were formed exclusively. The potential for stereocontrol by increasing the bulk of silicon substituents was limited for five-membered rings and good for six-membered rings. Phenylsilanes were found to participate in cyclization.

Original languageEnglish (US)
Pages (from-to)2821-2829
Number of pages9
JournalTetrahedron
Volume42
Issue number11
DOIs
StatePublished - 1986

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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