(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

doi:10.1021/ol990402f

(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: Contribution to journal › Article › peer-review

89 Scopus citations

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.

Original language	English (US)
Pages (from-to)	747-750
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	6
DOIs	https://doi.org/10.1021/ol990402f
State	Published - Mar 23 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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(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. / Soloshonok, Vadim A.; Cai, Chaozhong; Hruby, Victor J.
In: Organic Letters, Vol. 2, No. 6, 23.03.2000, p. 747-750.

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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 - Soloshonok, Vadim A.

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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(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

Abstract

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