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Synthesis of Substituted 5‐(Pyrrolidin‐2‐yl)tetrazoles and Their Application in the Asymmetric Biginelli Reaction
Author(s) -
Wu YongYong,
Chai Zhuo,
Liu XinYuan,
Zhao Gang,
Wang ShaoWu
Publication year - 2009
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.200801046
Subject(s) - chemistry , biginelli reaction , catalysis , enantioselective synthesis , reaction conditions , combinatorial chemistry , organic chemistry , medicinal chemistry
A series of chiral substituted 5‐(pyrrolidin‐2‐yl)tetrazoles have been synthesized and evaluated as organocatalysts for the asymmetric Biginelli reaction. The relationship between catalytic activity and the different catalyst structures is briefly discussed. By using the optimized catalyst C 10 (10 mol‐%), a series of 3,4‐dihydropyrimidin‐2(1 H )‐one (DHPM) derivatives have been obtained in 63–88 % yields and 68–81 % ee values within 24 h at room temperature. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)