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Synfacts 2007(2): 0212-0212  
DOI: 10.1055/s-2006-955788
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Direct Aza-Hetero-Diels-Alder Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
H. Liu, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong*
University of Science and Technology of China, Hefei, Chengdu Institute of Organic Chemistry, and Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China
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Publikationsdatum:
23. Januar 2007 (online)

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Significance

An enantioselective direct aza-­Diels-Alder reaction between cyclohexenone 1 and aromatic aldimines 2 is described. The formation of various aromatic substituted isoquinuclidines 3 is efficiently catalyzed by phosphoric acid 4, derived from H8-binol. Compounds 3 were obtained in high yields with good enantioselectivites and moderate diastereomeric ratios. Brønsted acid catalyst 4 activates both aldimines 2 and enone 1 by shifting the equilibrium towards the dienol. Importantly, no enamine-generating catalyst or second Brønsted acid was needed. Additionally, the authors described a one-pot, three-component reaction between cyclohexenone 1, aldehydes 5 and p-anisidine 6.