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

Gunda I. Georg

doi:10.1016/S0040-4039(01)91165-7

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

Gunda I. Georg

Medicinal Chemistry

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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 language	English (US)
Pages (from-to)	3779-3782
Number of pages	4
Journal	Tetrahedron Letters
Volume	25
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(01)91165-7
State	Published - 1984

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title = "Stereoselective synthesis of 3-(1-Hydroxyethyl)-2-azetidinonesfrom 3-hydroxybutyrates",

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.",

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T1 - Stereoselective synthesis of 3-(1-Hydroxyethyl)-2-azetidinonesfrom 3-hydroxybutyrates

AU - Georg, Gunda I.

PY - 1984

Y1 - 1984

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

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