The zinc mediated condensation of amino acid esters with imines to β- lactams

J.T.B.H. Jastrzebski; G. Van Koten

doi:10.1016/S0960-894X(01)80954-9

The zinc mediated condensation of amino acid esters with imines to β- lactams

J.T.B.H. Jastrzebski, G. Van Koten

Sub Organic Chemistry and Catalysis

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

An experimentally attractive stereoselective 'one pot' synthesis of β- lactams is described. This route is based on the zinc mediated condensation of an α-amino acid ester with an imine via a zinc ester enolate. Making use of proper substituents in both the amino acid ester and the imine the stereochemistry of the C-C bond forming step can be completely controlled.

Original language	English
Pages (from-to)	2351-2356
Number of pages	6
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	3
Issue number	11
DOIs	https://doi.org/10.1016/S0960-894X(01)80954-9
Publication status	Published - 12 Mar 1993

Keywords

2 azetidinone derivative
beta lactam derivative
article
drug synthesis
reaction analysis
stereochemistry

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10.1016/S0960-894X(01)80954-9

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abstract = "An experimentally attractive stereoselective 'one pot' synthesis of β- lactams is described. This route is based on the zinc mediated condensation of an α-amino acid ester with an imine via a zinc ester enolate. Making use of proper substituents in both the amino acid ester and the imine the stereochemistry of the C-C bond forming step can be completely controlled.",

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AU - Van Koten, G.

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N2 - An experimentally attractive stereoselective 'one pot' synthesis of β- lactams is described. This route is based on the zinc mediated condensation of an α-amino acid ester with an imine via a zinc ester enolate. Making use of proper substituents in both the amino acid ester and the imine the stereochemistry of the C-C bond forming step can be completely controlled.

AB - An experimentally attractive stereoselective 'one pot' synthesis of β- lactams is described. This route is based on the zinc mediated condensation of an α-amino acid ester with an imine via a zinc ester enolate. Making use of proper substituents in both the amino acid ester and the imine the stereochemistry of the C-C bond forming step can be completely controlled.

KW - 2 azetidinone derivative

KW - beta lactam derivative

KW - article

KW - drug synthesis

KW - reaction analysis

KW - stereochemistry

U2 - 10.1016/S0960-894X(01)80954-9

DO - 10.1016/S0960-894X(01)80954-9

M3 - Article

SN - 0960-894X

VL - 3

SP - 2351

EP - 2356

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 11

ER -

The zinc mediated condensation of amino acid esters with imines to β- lactams

Abstract

Keywords

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