Abstract
The enantioselective addition of diethylzinc to benzaldehyde has been used as standard procedure to test a series of new chiral catalysts derived from norbornane framework. The new ligands are β-amino alcohols possessing both heteroatomic substituents attached to the C(1) and C(2)- endo positions (novel non-coplanar disposition) of a 3,3-dimethylsubstituted norbornane. The results obtained, compared with other previously reported on the related C(2)- exo-7,7-dimethyl series, demonstrate that the relative disposition of the amino, hydroxy and gem-dimethyl groups, as well as the N-alkyl substituents, play an important role on the catalytic activity. Interesting transition-state models have been also proposed in order to explain the observed experimental results.
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