Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation

Vladimir Gevorgyan, Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Brφnsted acid catalyzed or Bu4NF-TiCl4 mediated cyclization of (Z)-ω-stannyl ether aldehyde 1a gives 2a, whereas (E)-isomer 1b affords 2b. To explain this stereochemical outcome, a push mechanism is proposed.

Original languageEnglish
Pages (from-to)1313-1316
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number8
DOIs
Publication statusPublished - Feb 19 1993
Externally publishedYes

Fingerprint

Cyclization
Aldehydes
Isomers
Ether
Condensation
Acids
titanium tetrachloride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation. / Gevorgyan, Vladimir; Kadota, Isao; Yamamoto, Yoshinori.

In: Tetrahedron Letters, Vol. 34, No. 8, 19.02.1993, p. 1313-1316.

Research output: Contribution to journalArticle

Gevorgyan, Vladimir ; Kadota, Isao ; Yamamoto, Yoshinori. / Cyclic transition state in the acid catalyzed intramolecular allylstannane-aldehyde condensation. In: Tetrahedron Letters. 1993 ; Vol. 34, No. 8. pp. 1313-1316.
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