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Cooperative and Enantioselective NbCl 5 /Primary Amine Catalyzed Biginelli Reaction
Author(s) -
Cai YongFeng,
Yang HuaMeng,
Li Li,
Jiang KeZhi,
Lai GuoQiao,
Jiang JianXiong,
Xu LiWen
Publication year - 2010
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.201000894
Subject(s) - chemistry , lewis acids and bases , enantioselective synthesis , amine gas treating , catalysis , biginelli reaction , yield (engineering) , organic chemistry , primary (astronomy) , lewis acid catalysis , organocatalysis , combinatorial chemistry , materials science , physics , astronomy , metallurgy
A series of chiral organocatalysts and Lewis acids have been evaluated in the Lewis acid/organocatalysts‐based cooperative catalytic Biginelli reaction, which resulted in the determination of a novel cooperative Lewis acid/primary amine catalyst system, NbCl 5 /QN‐NH 2 . The synergistic effect of NbCl 5 and the quinine‐derived primary amine is pronounced and gave dihydropyrimidiones (DHPMs) in moderate to good enantioselectivities (up to 84 % ee ) and good to excellent yields (up to 99 % yield) under mild conditions.
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