[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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32 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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Bearings (structural)
Stereochemistry
Enantiomers
Genetic Recombination
stannane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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author = "Katsuhiko Tomooka and Tatsuya Igarashi and Takeshi Nakai",
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AU - Nakai, Takeshi

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AB - 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.

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