[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

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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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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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