Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes
- 23 February 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (6) , 869-872
- https://doi.org/10.1021/ol015505o
Abstract
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%.Keywords
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