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

J. Am. Chem. Soc., 129 (6), 1480 -1481, 2007. 10.1021/ja0658766 S0002-7863(06)05876-8
Web Release Date: January 19, 2007

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

Jorge Esquivias, Ramón Gómez Arrays,* and Juan C. Carretero*

Departamento de Química Orgnica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

ramon.gomez@uam.es; juancarlos.carretero@uam.es

Received August 13, 2006

Abstract:

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 Ni^II-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.

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