STEREOCHEMICAL FEATURES OF THE STEREOSELECTIVE INTERACTION BETWEEN (R)--7,7'-BIS(1-PROPEN)-3-OXY)-2,2'-DIHYDROXY-1,1'-BINAPHTYL OR (S)-7,7'-BIS(1-PROPEN)-3-OXY)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL AND QUININE

被引:8
作者
UCCELLOBARRETTA, G [1 ]
PINI, D [1 ]
ROSINI, C [1 ]
SALVADORI, P [1 ]
机构
[1] CNR,CTR STUDIO MACROMOLEC STEREORDINATE OTTICAMENTE A,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY
关键词
D O I
10.1016/0021-9673(94)80416-8
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Quinine forms diastereoisomeric adducts with the enantiomers of 7,7'-bis(1-propen-3-oxy)-2,2'-dihydroxy-1,1'-binaphthyl. Their stereochemistry in solution was investigated by H-1 NMR spectroscopy at various temperatures and by analysis of the intermolecular H-1{H-1} nuclear Overhauser effect enhancements. A hypothesis for the chiral discrimination mechanism involved in the HPLC separation of this binaphthyl compound on a quinine-based chiral stationary phase is given.
引用
收藏
页码:541 / 548
页数:8
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