Download PDF
Synfacts 2007(1): 0093-0093  
DOI: 10.1055/s-2006-955665
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

First Organocatalytic Asymmetric Biginelli Reaction

Contributor(s): Benjamin List, Corinna Reisinger
X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong*
University of Science and Technology of China, Hefei, Chengdu Institute of Organic Chemistry and , Graduate School of the Chinese Academy of Sciences, Beijing, P. R. of China
Further Information

Publication History

Publication Date:
15 December 2006 (online)

   Permissions and Reprints

Significance

The first highly enantioselective organocatalytic Biginelli reaction is described. Starting from an aldehyde (1), thiourea, and various ace­toacetates (2), this acid-catalyzed multicomponent reaction furnishes thio-analogues of diversely substituted 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) (3), in moderate to good yields and high enantioselectivities. As chiral Brønsted acid organocatalyst the authors employed a binol-derived phosphoric acid. Moreover, three examples of the use of urea instead of thiourea are shown to obtain original DHPMs rather than the thio-analogues. Furthermore, an application in the synthesis of the drug monastrol is reported.