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

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Jorge Esquivias, Ramón Gómez Arrayás,* and Juan C. Carretero*;

Departamento de Qumica Orgnica, Facultad de Ciencias, Universidad Autnoma de Madrid, Cantoblanco, 28049 Madrid, Spain

J. Am. Chem. Soc., 2007, 129 (6), pp 1480–1481

DOI: 10.1021/ja0658766

Publication Date (Web): January 19, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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

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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Published In Issue February 14, 2007
Received August 13, 2006

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Communication

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Chiral Brønsted Acid-Catalyzed Inverse Electron-Demand Aza Diels−Alder Reaction Chiral Brønsted Acid-Catalyzed Inverse Electron-Demand Aza Diels−Alder Reaction

Diastereoselective Diels−Alder Reactions of N-Sulfonyl-1-aza-1,3-butadienes with Optically Active Enol Ethers: An Asymmetric Variant of the 1-Azadiene Diels−Alder Reaction

Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes

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