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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, Email: ramon.gomezuam.es, juancarlos.carreterouam.es

J. Esquivias, R. G. Arrayas, J. C. Carretero, J. Am. Chem. Soc., 2007, 129, 1480-1481.

DOI: 10.1021/ja0658766 (free Supporting Information)


Abstract

An efficient chiral Lewis acid-catalyzed inverse-electron-demand Diels-Alder reaction of N-sulfonyl 1-aza-1,3-dienes is based on the combination of Ni(II)-DBFOX complex as catalyst and the use of a metal-coordinating (8-quinolyl)sulfonyl moiety. The reaction provides highly functionalized piperidine derivatives in good yields with excellent endo-selectivity, and good enantioselectivities.

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Key Words

Diels-Alder reaction, N-Heterocycles


ID: J48-Y2007-0340