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

14 Citations (Scopus)

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

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Lewis Acids
Biomimetics
Cyclization
Alkylation
Aldehydes
titanium tetrafluoride

Keywords

  • Aldehydes
  • Allylsilane
  • Biomimetic reactions
  • Cyclization
  • TiF

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes. / Anastasia, Luigi; Giannini, Elios; Zanoni, Giuseppe; Vidari, Giovanni.

In: Tetrahedron Letters, Vol. 46, No. 35, 29.08.2005, p. 5803-5806.

Research output: Contribution to journalArticle

Anastasia, Luigi ; Giannini, Elios ; Zanoni, Giuseppe ; Vidari, Giovanni. / TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 35. pp. 5803-5806.
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