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Synthesis of New C 2 ‐Symmetric Chiral Bisamides from (1 S ,2 S )‐Cyclohexane‐1,2‐dicarboxylic Acid
Author(s) -
Zhou Chan,
Xu Jiaxi
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400005
Subject(s) - cyclohexane , chemistry , hydrogenolysis , benzaldehyde , medicinal chemistry , imine , dicarboxylic acid , organic chemistry , catalysis
A series of new C 2 ‐symmetric (1 S ,2 S )‐cyclohexane‐1,2‐dicarboxamides was synthesized from (1 S ,2 S )‐cyclohexane‐1,2‐dicarbonyl dichloride and N ‐benzyl‐substituted aromatic amines, which were prepared from 2‐aminopyridine, 2‐chloroaniline, and 2‐aminophenol via imine formation with benzaldehyde and subsequent reduction with NaBH 4 . (1 S ,2 S )‐ N , N ′‐Dibenzyl‐ N , N ′‐bis[2‐(benzyloxy)phenyl]cyclohexane‐1,2‐dicarboxamide was converted to (1 S ,2 S )‐ N , N′ ‐dibenzyl‐ N , N ′‐bis(2‐hydroxyphenyl)cyclohexane‐1,2‐dicarboxamide via hydrogenolysis in the presence of Pd(OH) 2 on active carbon powder.