[1,2]-Wittig rearrangement of enantio-defined α- alkoxyalkyllithiums: Stereochemistry at the Li-bearing terminus and mutual recognition of enantiomers during the radical recombination

Katsuhiko Tomooka, Tatsuya Igarashi, Takeshi Nakai

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33 Citations (Scopus)

Abstract

The [1,2]-Wittig rearrangements of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs, generated from the enantio-enriched stannanes via Sn / Li exchange, are shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating center, and exhibit a significant level of mutual enantiomer recognition in the radical recombination process.

Original languageEnglish
Pages (from-to)8139-8142
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number50
DOIs
Publication statusPublished - Dec 10 1993
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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