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

SangWen Hon | Zendy; ChunHsin Li | Zendy; JenHuang Kuo | Zendy; Nivrutti B. Barhate | Zendy; YiHung Liu | Zendy; Yu Wang | Zendy; ChienTien Chen | Zendy

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

Author(s) -

SangWen Hon,

ChunHsin Li,

JenHuang Kuo,

Nivrutti B. Barhate,

YiHung Liu,

Yu Wang,

ChienTien Chen

Publication year - 2001

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol015505o

Subject(s) - chemistry , enantioselective synthesis , catalysis , phenylalanine , oxidative coupling of methane , valine , combinatorial chemistry , medicinal chemistry , stereochemistry , amino acid , organic chemistry , biochemistry

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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