Resolution of (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid using (1R,2R)-trans-cyclohexane-1,2-diamine

被引：6
|
作者：
Someshwar, Nagamalla [1 ]
Ramanathan, Chinnasamy Ramaraj [1 ]
机构：
[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
来源：
TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 20期
关键词：
ENANTIOSELECTIVE SYNTHESIS; DIETHYLZINC ADDITION; DERIVATIVES;
D O I：
10.1016/j.tetasy.2015.09.002
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A simple and efficient method has been developed to resolve (+/-)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylic acid [(+/-)-BINOL-3,3'-dicarboxylic acid] (+/-)-1 using inexpensive and readily accessible chiral resolving agent (1R,2R)-trans-cyclohexane-1,2-diamine 2. Enantiomers of BINOL-3,3'-dicarboxylic acid were obtained in good yields and enantiomeric purity, for example, (S)-(-)-1 was isolated in 34% yield with >99% ee and (R)-(+)-1 was obtained in 36% yield with >99% ee. The formation of diastereomeric salt A between (S)-BINOL-3,3'-dicarboxylic acid and (1R,2R)-trans-cyclohexane-1,2-diamine was ascertained by using IR, single crystal X-ray crystallography, and HRMS. (C) 2015 Elsevier Ltd. All rights reserved.
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收藏
页码：1209 / 1213
页数：5
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