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Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes

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journal contribution
posted on 23.02.2001, 00:00 by Sang-Wen Hon, Chun-Hsin Li, Jen-Huang Kuo, N. B. Barhate, Yi-Hung Liu, Yu Wang, Chien-Tien Chen
A series of chiral oxovanadium(IV) complexes derived from tridentate N-3,5-substituted and N-3,4-benzo- and N-5,6-benzo-salicylidene-α-amino acids can serve as efficient catalysts for the enantioselective oxidative couplings of various 3-, 6-, and 7-substituted 2-naphthols under O2. The best scenario involves the use of a vanadyl complex arising from 2-hydroxy-1-naphthaldehyde and valine (or phenylalanine) in CCl4, leading to BINOLs in good yields (75−100%) and with enantioselectivities of up to 68%.