Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde

Isao Kadota, Daigo Hatakeyama, Katsura Seki, Yoshinori Yamamoto

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The Lewis acid mediated reactions of allenylstannanes 1 and 13 gave trans cyclic ethers 3a and 14, respectively, with high stereoselectivities. The cyclization to 7 gave trans cyclic ether 9a. The treatment of propargylstannanes 2 and 8 with Lewis acids such as SnCl4, BuSnCl3, and ZnCl2·OEt2 induced isomerization to allenylmetal species, which underwent cyclization to the corresponding 6- and 5-membered cyclic ethers 3 and 9, respectively. The stereoselectivities dependend upon the ring size and Lewis acid utilized.

Original languageEnglish
Pages (from-to)3059-3062
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number17
DOIs
Publication statusPublished - Apr 22 1996
Externally publishedYes

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Cyclic Ethers
Lewis Acids
Aldehydes
Stereoselectivity
Cyclization
Isomerization

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde. / Kadota, Isao; Hatakeyama, Daigo; Seki, Katsura; Yamamoto, Yoshinori.

In: Tetrahedron Letters, Vol. 37, No. 17, 22.04.1996, p. 3059-3062.

Research output: Contribution to journalArticle

Kadota, Isao ; Hatakeyama, Daigo ; Seki, Katsura ; Yamamoto, Yoshinori. / Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 17. pp. 3059-3062.
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