Frontiers of Chemical Science and Engineering

, Volume 7, Issue 4, pp 408–414 | Cite as

Synthesis of C 1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction

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Abstract

Two new C 1-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.

Keywords

enantioselective Henry reaction C1-symmetric diamines asymmetric reaction nitroalkanol 
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Copyright information

© Higher Education Press and Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  1. 1.Key Laboratory of Systems Bioengineering, Ministry of Education, School of Chemical Engineering and TechnologyTianjin UniversityTianjinChina
  2. 2.State Key Laboratory of Elemento-Organic Chemistry, Department of ChemistryNankai UniversityTianjinChina

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