Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes

A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl·TMEDA has been developed. Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous ch...

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Bibliographic Details
Published in:Journal of organic chemistry 1999-04, Vol.64 (7), p.2264-2271
Main Authors: Nakajima, Makoto, Miyoshi, Irie, Kanayama, Kumiko, Hashimoto, Shun-ichi, Noji, Masahiro, Koga, Kenji
Format: Article
Language:English
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Summary:A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl·TMEDA has been developed. Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo981808t