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Highly Enantioselective Michael Addition of Cyclic 1,3‐Dicarbonyl Compounds to β,γ‐Unsaturated α‐Keto Esters
Author(s) -
Chen XingKuan,
Zheng ChangWu,
Zhao ShengLi,
Chai Zhuo,
Yang YingQuan,
Zhao Gang,
Cao WeiGuo
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000045
Subject(s) - chemistry , thiourea , enantioselective synthesis , michael reaction , coumarin , catalysis , amine gas treating , organic chemistry , tertiary amine , addition reaction , medicinal chemistry
A highly enantioselective Michael addition of cyclic 1,3‐dicarbonyl compounds to β,γ‐unsaturated α‐keto esters catalyzed by amino acid‐derived thiourea‐tertiary‐amine catalysts is presented. Using 5 mol% of a novel tyrosine‐derived thiourea catalyst, a series of chiral coumarin derivatives were obtained in excellent yields (up to 99%) and with up to 96% ee under very mild conditions within a short reaction time.
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