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Highly Enantioselective Biginelli Reaction Promoted by Chiral Bifunctional Primary Amine‐Thiourea Catalysts: Asymmetric Synthesis of Dihydropyrimidines
Author(s) -
Wang Yangyun,
Yang Haitao,
Yu Jipan,
Miao Zhiwei,
Chen Ruyu
Publication year - 2009
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.200900597
Subject(s) - chemistry , bifunctional , thiourea , enantioselective synthesis , amine gas treating , biginelli reaction , catalysis , organocatalysis , organic chemistry , dichloromethane , primary (astronomy) , combinatorial chemistry , medicinal chemistry , solvent , physics , astronomy
The diastereospecific formation of dihydropyrimidines (DHPMs) has been achieved in moderate to high yields with up to 99% ee by a Biginelli reaction. The reaction was performed by using a combined catalyst consisting of a chiral bifunctional primary amine‐thiourea 9f and a Brønsted acid with tert ‐butylammonium trifluoroacetate ( t‐ BuNH 2 ⋅TFA) as additive in dichloromethane at room temperature. The possible mechanism for the reaction has been proposed to explain the origin of the activation and the asymmetric induction.