Synthesis of C1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction
Synthesis of C1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction
Lili ZHANG1, Ming LIU1, Shijun MA2, Yaodong HUANG1(), Yongmei WANG2()
1. Key Laboratory of Systems Bioengineering, Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China; 2. State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, China
Two new C1-symmetric primary-secondary diamines were synthesized via the reaction of (S,S)-1,2-diphenyl ethylene diamine with 3,5-ditert-butyl salicylaldehyde and salicylaldehyde, respectively, followed by reduction with NaBH4. The combination of the ligand from 3,5-ditert-butyl salicylaldehyde with CuBr could effciently catalyze the Henry reaction to afford β-nitroalkanols in moderate to good yields (up to 87%) and high enantioselectivities (up to 88% ee). A possible mechanism of the reaction was proposed.
Corresponding Author(s):
HUANG Yaodong,Email:huangyaodong@tju.edu.cn; WANG Yongmei,Email:ymw@nankai.edu.cn
引用本文:
. Synthesis of C1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction[J]. Frontiers of Chemical Science and Engineering, 2013, 7(4): 408-414.
Lili ZHANG, Ming LIU, Shijun MA, Yaodong HUANG, Yongmei WANG. Synthesis of C1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction. Front Chem Sci Eng, 2013, 7(4): 408-414.
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