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Stereoelectronic influence on the NaBH4reduction stereoselectivity of alicyclic β-ketoesters

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
33
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(00)79562-1
Keywords
  • Hydride Reduction
  • Stereoselectivity
  • Ketoester
  • Stereoelectronic
  • Borohydride
Disciplines
  • Chemistry

Abstract

Abstract The stereochemistry of β-hydroxyesters produced in the NaBH 4 reduction of alicyclic β-ketoesters has been determined. An enhanced rate of reduction has been observed for those isomers in which the carboxylate is antiperiplanar to the hydride ion in the transition state.

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