A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones

V. A. Soloshonok; C. Cai; V. J. Hruby

doi:10.1016/S0040-4039(00)01737-8

A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones

V. A. Soloshonok, C. Cai, V. J. Hruby

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

71 Scopus citations

Abstract

The origin of virtually complete face diastereoselectivity in the organic base-catalyzed, room temperature Michael addition reactions between Ni(II)-complexes of Schiff bases of glycine and chiral 3-(E-enoyl)-4-substituted-1,3-oxazolidin-2-ones was shown to stem from the unusual mode of steric interactions in determining the corresponding transition state. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	9645-9649
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(00)01737-8
State	Published - Dec 2 2000
Externally published	Yes

Keywords

Amino acids
Asymmetric synthesis
Michael additions
Nickel(II) complex
Oxazolidin-2-ones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)01737-8

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title = "A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones",

abstract = "The origin of virtually complete face diastereoselectivity in the organic base-catalyzed, room temperature Michael addition reactions between Ni(II)-complexes of Schiff bases of glycine and chiral 3-(E-enoyl)-4-substituted-1,3-oxazolidin-2-ones was shown to stem from the unusual mode of steric interactions in determining the corresponding transition state. (C) 2000 Elsevier Science Ltd.",

keywords = "Amino acids, Asymmetric synthesis, Michael additions, Nickel(II) complex, Oxazolidin-2-ones",

author = "Soloshonok, {V. A.} and C. Cai and Hruby, {V. J.}",

note = "Funding Information: The work was supported by grants from the US Public Health Service Grant and the National Institute of Drug Abuse DA 06284, DA 13449 and DK 17420. The views expressed are those of the authors and not necessarily of the USPHS.",

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doi = "10.1016/S0040-4039(00)01737-8",

language = "English (US)",

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TY - JOUR

T1 - A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones

AU - Soloshonok, V. A.

AU - Cai, C.

AU - Hruby, V. J.

N1 - Funding Information: The work was supported by grants from the US Public Health Service Grant and the National Institute of Drug Abuse DA 06284, DA 13449 and DK 17420. The views expressed are those of the authors and not necessarily of the USPHS.

PY - 2000/12/2

Y1 - 2000/12/2

N2 - The origin of virtually complete face diastereoselectivity in the organic base-catalyzed, room temperature Michael addition reactions between Ni(II)-complexes of Schiff bases of glycine and chiral 3-(E-enoyl)-4-substituted-1,3-oxazolidin-2-ones was shown to stem from the unusual mode of steric interactions in determining the corresponding transition state. (C) 2000 Elsevier Science Ltd.

AB - The origin of virtually complete face diastereoselectivity in the organic base-catalyzed, room temperature Michael addition reactions between Ni(II)-complexes of Schiff bases of glycine and chiral 3-(E-enoyl)-4-substituted-1,3-oxazolidin-2-ones was shown to stem from the unusual mode of steric interactions in determining the corresponding transition state. (C) 2000 Elsevier Science Ltd.

KW - Amino acids

KW - Asymmetric synthesis

KW - Michael additions

KW - Nickel(II) complex

KW - Oxazolidin-2-ones

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DO - 10.1016/S0040-4039(00)01737-8

M3 - Article

AN - SCOPUS:0034598019

SN - 0040-4039

VL - 41

SP - 9645

EP - 9649

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones

Abstract

Keywords

ASJC Scopus subject areas

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