DIANANE-Cr(III)-salen Complexes as Highly Enantioselective Catalysts for Hetero-Diels-Alder Reactions of Aldehydes with Dienes

Albrecht Berkessel *, Nadine Vogl

*Institut für Organische Chemie, Universität zu Köln, Greinstr. 4, 50939 Köln, Germany, Email: berkesseluni-koeln.de

A. Berkessel, N. Vogl, Eur. J. Org. Chem., 2006, 5029-5035.

DOI: 10.1002/ejoc.200600359

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Abstract

A new type of chromium-salen complex bearing DIANANE (endo,endo-2,5-diaminonorbornane) has been applied to the hetero-Diels-Alder reaction of Danishefskys diene with various aldehydes. The reactions afford the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and enantioselectivities.

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A Highly Enantioselective Catalyst for the Asymmetric Nozaki-Hiyama-Kishi Reaction of Allylic and Vinylic Halides

A. Berkessel, D. Menche, C. A. Sklorz, M. Schroeder, I. Paterson, Angew. Chem., 2003, 115, 1062-1065.

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Key Words

Diels-Alder Reaction, 2,3-Dihydro-4H-pyran-4-ones

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ID: J24-Y2006-3730