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Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid
Author(s) -
Lu Nan,
Chen Dezhan,
Zhang Guiqiu,
Liu Qingjian
Publication year - 2011
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.22481
Subject(s) - chemistry , enantioselective synthesis , aldehyde , imine , nucleophile , biginelli reaction , tartaric acid , protonation , electrophile , organic chemistry , enantiomer , catalysis , organocatalysis , solvent , brønsted–lowry acid–base theory , medicinal chemistry , ion , citric acid
Abstract In this study, enantioselective Biginelli reaction of aldehyde, β‐ketoester, and urea catalyzed by natural (2 R , 3 R )‐tartaric acid has been investigated using density functional theory calculations. The results indicate that the most favorable pathway involves a protonated imine from aldehyde and urea in the first step. Tartaric acid forms H‐bonds network with substrates enhancing the electrophilicity of protonated imine and the nucleophilicity of β‐ketoester. ( R )‐3,4‐Dihydropyrimidin‐2‐(1 H )‐ones is preferable for the reaction. The solvent effect is discussed in the prediction of enantiomeric excess (ee) values in ethanol and water. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2011