Synthesis and catalytic activity of 10-(aminomethyl)isoborneol-based catalysts: the role of the C(2)-group on the asymmetric induction

Five enantiopure C(2)-substituted 10-[(dimethylamino)methyl]isoborneols has been prepared by a novel straightforward camphor-based route, and probed as δ-amino-alcohol ligands for the enantioselective addition of diethylzinc to benzaldehyde. The established route constitutes a divergent model proced...

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Published in:Tetrahedron: asymmetry 2003-07, Vol.14 (14), p.1959-1963
Main Authors: Garcı́a Martı́nez, Antonio, Teso Vilar, Enrique, Garcı́a Fraile, Amelia, de la Moya Cerero, Santiago, Lora Maroto, Beatriz
Format: Article
Language:English
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Summary:Five enantiopure C(2)-substituted 10-[(dimethylamino)methyl]isoborneols has been prepared by a novel straightforward camphor-based route, and probed as δ-amino-alcohol ligands for the enantioselective addition of diethylzinc to benzaldehyde. The established route constitutes a divergent model procedure for this class of δ-amino-isoborneol ligands, allowing different substitutions, not only at the nitrogen atom, but also at the more interesting hydroxyl-bearing C(2)–norbornane position. This last synthetic possibility has made possible a study of the role played by the group located at the C(2)–norbornane position on the catalytic activity. New catalyst models and transition-state models for explaining such a role are also proposed and discussed. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(03)00411-7