An Enantioselective Biginelli Reaction Catalyzed by a Simple Chiral Secondary Amine and Achiral Brønsted Acid by a Dual‐Activation Route
- 18 March 2008
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 14 (10), 3177-3181
- https://doi.org/10.1002/chem.200701581
Abstract
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 Brønsted 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.This publication has 62 references indexed in Scilit:
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