期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 10, 页码 3177-3181出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200701581
关键词
asymmetric catalysis; Biginelli reaction; dual activation; multicomponent reactions; pyrimidines; reaction mechanisms
An enantioselective Biginelli reaction that proceeds by a dual-activation route has been developed by using a combined catalyst of a readily available trans-4-hydroxyproline-derived secondary amine and a Bronsted acid. Aromatic, heteroaromatic, and fused-ring aldehydes were found to be suitable substrates for this multicomponent reaction. The corresponding dihydropyrimidines were obtained in moderate-to-good yields with up to 98% ee under mild conditions. Based on the experimental results and the observed absolute configurations of the products, a plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.
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