(S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Ideal Michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives

Vadim A. Soloshonok, Chaozhong Cai, Victor J. Hruby

Research output: Research - peer-reviewArticle

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Abstract

(figure presented) Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases. Virtually complete control of simple and face diastreoselectivity, observed in these reactions, combined with quantitative chemical yields renders this methodology synthetically superior to the previous methods.

LanguageEnglish (US)
Pages747-750
Number of pages4
JournalOrganic Letters
Volume2
Issue number6
StatePublished - Mar 23 2000

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Oxazolidinones
Addition reactions
Schiff Bases
Glycine
Derivatives
glycine
imines
methodology

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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abstract = "(figure presented) Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases. Virtually complete control of simple and face diastreoselectivity, observed in these reactions, combined with quantitative chemical yields renders this methodology synthetically superior to the previous methods.",
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AU - Cai,Chaozhong

AU - Hruby,Victor J.

PY - 2000/3/23

Y1 - 2000/3/23

N2 - (figure presented) Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases. Virtually complete control of simple and face diastreoselectivity, observed in these reactions, combined with quantitative chemical yields renders this methodology synthetically superior to the previous methods.

AB - (figure presented) Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases. Virtually complete control of simple and face diastreoselectivity, observed in these reactions, combined with quantitative chemical yields renders this methodology synthetically superior to the previous methods.

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