Stereoselective synthesis of 3-(1-Hydroxyethyl)-2-azetidinonesfrom 3-hydroxybutyrates

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Abstract

Addition of dianions of 3-hydroxybutyrates to benzylideneaniline results in direct formation of trans S*-3-(l-hydroxyethyl)-1,4-diphenyl-2-azetidinone with 95% diastereoselectivity. Inversion of the configuration at Cα, gives the desired trans R*-2-azetidinone in high yield.

Original languageEnglish (US)
Pages (from-to)3779-3782
Number of pages4
JournalTetrahedron Letters
Volume25
Issue number35
DOIs
StatePublished - 1984

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