Catalytic Asymmetric Coupling of 2-Naphthols by Chiral Tridentate Oxovanadium(IV) Complexes
Organic Letters2001Vol. 3(6), pp. 869–872
Citations Over TimeTop 10% of 2001 papers
Sang‐Wen Hon, Chun‐Hsin Li, Jen‐Huang Kuo, Nivrutti B. Barhate, Yi‐Hung Liu, Yu Wang, Chien‐Tien Chen
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-alpha-amino acids can serve as efficient catalysts for the enantioselective oxidative couplings of various 3-, 6-, and 7-substituted 2-naphthols under O(2). The best scenario involves the use of a vanadyl complex arising from 2-hydroxy-1-naphthaldehyde and valine (or phenylalanine) in CCl(4), leading to BINOLs in good yields (75-100%) and with enantioselectivities of up to 68%.
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