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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
37
Issue
41
Identifiers
DOI: 10.1016/0040-4039(96)01684-x
Disciplines
  • Chemistry

Abstract

Abstract Treatment of RCH(OMEM)CFBr 2 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.

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