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Chiral Copper Complexes of Phosphino Sulfenyl Ferrocenes as Efficient Catalysts for Enantioselective Formal Aza Diels−Alder Reactions of N-Sulfonyl Imines

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Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid
Cite this: J. Am. Chem. Soc. 2004, 126, 2, 456–457
Publication Date (Web):December 20, 2003
https://doi.org/10.1021/ja038494y
Copyright © 2004 American Chemical Society

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    Abstract

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    In the presence of a catalytic amount of silver perchlorate, copper(I) bromide complexes of planar chiral 1-phosphino-2-sulfenylferrocenes behave as very efficient chiral Lewis acids catalysts in the formal Aza Diels−Alder reaction of N-arylsulfonyl aldimines with electron-rich dienes (Danishefsky's and related dienes). Mixing of equimolar amounts of the readily available enantiopure ferrocenyl P,S-bidentate ligand and CuBr quantitatively affords the precatalyst Cu complex as an air-stable solid. This catalytic asymmetric procedure has a broad structural scope:  aldimines of aromatic, α,β-unsaturated, and even enolizable aliphatic aldehydes have been successfully used. The corresponding 2,3-dihydro-4-pyridones were obtained in good yields (57−90%) and with homogeneously high enantioselectivity (82−97% ee).

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