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Asymmetric Michael Addition of Cyclohexanone or Cyclopentanone to Chalcones Catalyzed by an L ‐Proline‐Based Organic Phosphane
Author(s) -
Liu Lingyan,
Zhu Yunna,
Huang Kaimeng,
Chang Weixing,
Li Jing
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201609
Subject(s) - cyclopentanone , cyclohexanone , chemistry , michael reaction , catalysis , diastereomer , adduct , proline , organocatalysis , organic chemistry , medicinal chemistry , enantioselective synthesis , biochemistry , amino acid
An organophosphane catalyst derived from L ‐proline was shown to be a very effective catalyst for asymmetric Michael addition reactions of various chalcones to cyclic ketones including both cyclohexanone and cyclopentanone. The corresponding adducts could be obtained in high yields (up to 91 %) and with excellent enantioselectivities (up to 99 % ee ) and diastereomeric ratios (up to >99:1). A possible catalytic mechanism, based on 31 P NMR and ESI‐MS observations, for this organophosphane‐catalyzed Michael addition has been proposed.