Catalytic Asymmetric Inverse-Electron-Demand Diels−Alder Reaction of N-Sulfonyl-1-Aza-1,3-Dienes

An efficient chiral Lewis acid-catalyzed inverse-electron-demand Diels−Alder reaction of 1-azadienes is described. This procedure is based on the combination of NiII-DBFOX complex as catalyst and the use of a metal-coordinating (8-quinolyl)sulfonyl moiety at the iminic nitrogen of the N-sulfonyl 1-a...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-02, Vol.129 (6), p.1480-1481
Main Authors: Esquivias, Jorge, Arrayás, Ramón Gómez, Carretero, Juan C
Format: Article
Language:English
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Summary:An efficient chiral Lewis acid-catalyzed inverse-electron-demand Diels−Alder reaction of 1-azadienes is described. This procedure is based on the combination of NiII-DBFOX complex as catalyst and the use of a metal-coordinating (8-quinolyl)sulfonyl moiety at the iminic nitrogen of the N-sulfonyl 1-aza-1,3-diene, providing highly functionalized piperidine derivatives in good yields with excellent endo-selectivity, and enantioselectivities typically in the range of 77−92% ee.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0658766