[2,3]Wittig rearrangement of enantiomerically-defined α-(allyloxy)stannanes

Solid evidence for inversion of configuration at the lithium- bearing migrating terminus

Katsuhiko Tomooka, Tatsuya Igarashi, Masashi Watanabe, Takeshi Nakai

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

The [2,3]Wittig rearrangement of enantiomerically-defined α-(allyloxy)stannanes, prepared from (S)-1-tributylstannyl-1-propanol, with butyllithium is shown to proceed with essentially complete inversion of configuration at the lithium-bearing migrating terminus. This inversion stereochemistry is further confirmed by the rearrangement of diastereomerically-defined α-(allyloxy)stannanes.

Original languageEnglish
Pages (from-to)5795-5798
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number39
DOIs
Publication statusPublished - Sep 22 1992
Externally publishedYes

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Bearings (structural)
Lithium
1-Propanol
Stereochemistry
stannane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

[2,3]Wittig rearrangement of enantiomerically-defined α-(allyloxy)stannanes : Solid evidence for inversion of configuration at the lithium- bearing migrating terminus. / Tomooka, Katsuhiko; Igarashi, Tatsuya; Watanabe, Masashi; Nakai, Takeshi.

In: Tetrahedron Letters, Vol. 33, No. 39, 22.09.1992, p. 5795-5798.

Research output: Contribution to journalArticle

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