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Highly Enantioselective Michael Addition of Malonate Derivatives to Enones Catalyzed by an N , N ′‐Dioxide–Scandium(III) Complex
Author(s) -
Chen Donghui,
Chen Zhenling,
Xiao Xiao,
Yang Zhigang,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901157
Subject(s) - enantioselective synthesis , scandium , yield (engineering) , catalysis , michael reaction , malonate , ligand (biochemistry) , chemistry , chalcone , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , biochemistry , receptor , metallurgy
A highly enantioselective Michael addition of malonate derivatives to chalcone derivatives catalyzed by an N , N′ ‐dioxide–Sc III complex was developed, which tolerated a broad range of substrates in moderate to excellent yield with 96–99 % ee. The reaction proceeded well in EtOH or water and could be scaled to grams in good yield with 98 % ee using only 1 mol % ligand L –scandium(III) complex as a catalyst (see scheme).