A novel method for the synthesis of ( R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid by asymmetric oxidative coupling of a chiral β-naphthol derivative catalyzed by CuCl

Asymmetric oxidative coupling of ( S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded ( S, S, R)-2,2′-dihydroxy-3,3′-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1′-binapthalene 2 with diastereomeric excess up to 65.9%. ( R)-BINOL-3,3′-diaci...

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Published in:Tetrahedron: asymmetry 2002-09, Vol.13 (17), p.1937-1940
Main Authors: Xin, Zhuo-qun, Da, Chao-shan, Dong, Shou-liang, Liu, Da-xue, Wei, Jie, Wang, Rui
Format: Article
Language:English
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Summary:Asymmetric oxidative coupling of ( S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded ( S, S, R)-2,2′-dihydroxy-3,3′-bis(2-methoxycarbonyl-1-pyrrolidinylcarbonyl)-1,1′-binapthalene 2 with diastereomeric excess up to 65.9%. ( R)-BINOL-3,3′-diacid 3 was obtained in 30% overall yield and 97% e.e. by separating the diastereomers and hydrolyzing 2. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(02)00507-4