Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

Masaki Shimizu, Yoko Takebe, Manabu Kuroboshi, Tamejiro Hiyama

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Abstract

Treatment of RCH(OMEM)CFBr2 with n-BuLi at -130°C in the presence of 4-heptanone gives the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of the chelation between lithium and oxygen atoms of the MEM group. Starting with 2-phenylpropanal, a product is produced highly selectively containing three contiguous stereocenters including a -CFBr- moiety.

Original languageEnglish
Pages (from-to)7387-7390
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number41
DOIs
Publication statusPublished - Oct 7 1996

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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