[1,2]-Wittig rearrangement of enantio-defined α-alkoxyalkyllithiums: Structural requirement and steric course at the Li-bearing terminus.

Katsuhiko Tomooka, Tatsuya Igarashi, Takeshi Nakai

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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)5927-5932
Number of pages6
JournalTetrahedron
Volume50
Issue number20
DOIs
Publication statusPublished - 1994
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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