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Catalytic asymmetric conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones with bifunctional catalysts.

ABSTRACT: In this communication, we describe an unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds that are otherwise difficult to prepare by asymmetric catalysis. The successful development of this reaction resulted from a discovery that, upon proper modification, a cinchona alkaloid bearing a thiourea functionality at 6' position can afford highly efficient catalysis for asymmetric conjugate additions.

SUBMITTER: Liu Y

PROVIDER: S-EPMC2730660 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Catalytic asymmetric conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones with bifunctional catalysts.

Liu Yan Y Sun Bingfeng B Wang Baomin B Wakem Matthew M Deng Li L

Journal of the American Chemical Society 20090101 2

In this communication, we describe an unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds that are otherwise difficult to prepare by asymmetric catalysis. The successful development of this reaction resulted from a discovery that, upon proper modifi ...[more]

PMID: 19113850

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