TiCl4 promoted reaction of aldehydes with 1,5-dienyl allylsilanes: Addition accompanied by cyclization

Giovanni Vidari, Maria Pia Bonicelli, Luigi Anastasia, Giuseppe Zanoni

Research output: Contribution to journalArticle

Abstract

TICl4 readily promotes the addition of 1,5-dienyl allylsilanes to aliphatic aldehydes with concomitant cyclization to afford 1,3-cis- disubstituted methylenecyclohexanes with remarkable stereoselectivity. The trimethylsilyl group exerts a strong activating and directing influence on the regioselectivity and stereoselectivity of this biomimetic cyclization. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3471-3474
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number18
DOIs
Publication statusPublished - Apr 29 2000

Keywords

  • Aldehydes
  • Biomimetic reactions
  • Cyclization
  • Dienes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Fingerprint Dive into the research topics of 'TiCl4 promoted reaction of aldehydes with 1,5-dienyl allylsilanes: Addition accompanied by cyclization'. Together they form a unique fingerprint.

  • Cite this