Synfacts 2008(4): 0396-0396  
DOI: 10.1055/s-2008-1042791
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

N,N′-Dioxide-Sc(III) Catalyst for Enantioselective Aza-Diels-Alder Reaction

Contributor(s): Mark Lautens, Valentina Aureggi
D. Shang, J. Xin, Y. Liu, X. Zhou, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
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19. März 2008 (online)


The development of a new chiral l-proline-derived N,N′-dioxide-scandium(III) catalyst for an efficient enantioselective aza-Diels-Alder reaction is reported. The corresponding 2,5-disubstituted dihydropyridinone products, from aldimines and a Danishefsky-type diene, are obtained with up to 92% yield and 92% ee.