Metal directed stereoselective synthesis of 3-(1′-hydroxyethyl)-2-azetidinones from ethyl 3-hydroxybutyrate

Gunda I. Georg; Eyüp Akgün

doi:10.1016/S0040-4039(00)89040-1

Metal directed stereoselective synthesis of 3-(1′-hydroxyethyl)-2-azetidinones from ethyl 3-hydroxybutyrate

Gunda I. Georg, Eyüp Akgün

Medicinal Chemistry

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Abstract

The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with N-anisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of tert-butyl magnesium chloride to the reaction mixture produced the rel(1′R,3R,4S)-3-(1′hydroxyethyl)-2-azetidinone 9, whereas the addition of triethylborane gave solely the rel(1′R,3R,4R) derivative 10.

Original language	English (US)
Pages (from-to)	3267-3270
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(00)89040-1
State	Published - 1990

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title = "Metal directed stereoselective synthesis of 3-(1′-hydroxyethyl)-2-azetidinones from ethyl 3-hydroxybutyrate",

abstract = "The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with N-anisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of tert-butyl magnesium chloride to the reaction mixture produced the rel(1′R,3R,4S)-3-(1′hydroxyethyl)-2-azetidinone 9, whereas the addition of triethylborane gave solely the rel(1′R,3R,4R) derivative 10.",

author = "Georg, {Gunda I.} and Ey{\"u}p Akg{\"u}n",

year = "1990",

doi = "10.1016/S0040-4039(00)89040-1",

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journal = "Tetrahedron Letters",

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AU - Georg, Gunda I.

AU - Akgün, Eyüp

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Y1 - 1990

N2 - The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with N-anisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of tert-butyl magnesium chloride to the reaction mixture produced the rel(1′R,3R,4S)-3-(1′hydroxyethyl)-2-azetidinone 9, whereas the addition of triethylborane gave solely the rel(1′R,3R,4R) derivative 10.

AB - The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with N-anisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of tert-butyl magnesium chloride to the reaction mixture produced the rel(1′R,3R,4S)-3-(1′hydroxyethyl)-2-azetidinone 9, whereas the addition of triethylborane gave solely the rel(1′R,3R,4R) derivative 10.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Metal directed stereoselective synthesis of 3-(1′-hydroxyethyl)-2-azetidinones from ethyl 3-hydroxybutyrate

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