TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

Luigi Anastasia, Elios Giannini, Giuseppe Zanoni, Giovanni Vidari

Research output: Contribution to journalArticle

Abstract

TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.

Original languageEnglish
Pages (from-to)5803-5806
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number35
DOIs
Publication statusPublished - Aug 29 2005

Keywords

  • Aldehydes
  • Allylsilane
  • Biomimetic reactions
  • Cyclization
  • TiF

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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