期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 352, 期 5, 页码 827-832出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900764
关键词
bifunctional thioureas; Michael addition; nitroolefins; organic catalysis; pyrazolin-5-ones
资金
- National Natural Science Foundation of China [20802074]
The first organocatalytic diastereo- and enantioselective Michael addition reaction of 4-substituted-pyrazolin-5-ones to nitroolefins has been developed with a chiral bifunctional thiourea as organocatalyst. A wide variety of desired multi-substituted pyrazolin-5-one derivatives with contiguous quaternary and tertiary stereocenters are smoothly obtained in very good yields (up to 98%) with excellent enantioselectivities (up to > 99% ee) and acceptable diastereoselectivities (up to 80:20). This experimentally simple process facilitates the access to various enantioenriched, multiply substituted pyrazolin-5-one derivatives, potential biologically active molecules, starting from readily available starting materials.
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