Synthesis of New C2‐Symmetric Chiral Bisamides from (1S,2S)‐Cyclohexane‐1,2‐dicarboxylic Acid |
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| Authors: | Chan Zhou Jiaxi Xu |
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| Affiliation: | State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P.?R. China, (phone/fax: +86‐10‐64435565) |
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| Abstract: | A series of new C2‐symmetric (1S,2S)‐cyclohexane‐1,2‐dicarboxamides was synthesized from (1S,2S)‐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 NaBH4. (1S,2S)‐N,N′‐Dibenzyl‐N,N′‐bis[2‐(benzyloxy)phenyl]cyclohexane‐1,2‐dicarboxamide was converted to (1S,2S)‐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. |
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| Keywords: | Bisamides Cyclohexane‐1,2‐dicarboxylic acid Henry reaction |
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