Catalytic asymmetric conjugate addition of various α-mercaptoketones to α,β-unsaturated N-acylated oxazolidin-2-ones with bifunctional organocatalyst

A bifunctional squaramide catalysed enantioselective conjugate Michael addition reaction of various alpha -mercaptoketones to alpha , beta -unsaturated N-acylated oxazolidinones under mild reaction conditions has been developed. This catalytic reaction afforded the corresponding adducts in good yiel...

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Bibliographic Details
Published inRSC advances Vol. 4; no. 52; pp. 27346 - 27353
Main Authors Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published 01.01.2014
Subjects
Adducts
Asymmetry
Catalysis
Catalysts
catalytic activity
chemical reactions
Conjugates
enantioselectivity
organocatalysts
oxazolidinones
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Summary:A bifunctional squaramide catalysed enantioselective conjugate Michael addition reaction of various alpha -mercaptoketones to alpha , beta -unsaturated N-acylated oxazolidinones under mild reaction conditions has been developed. This catalytic reaction afforded the corresponding adducts in good yields with high enantioselectivities (up to 92% ee). This is the first example of organocatalysed sulfa-Michael addition using various alpha -mercaptoketones as the Michael donors.
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ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA02400A