Synthesis of C₁-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction

Abstract

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.

Keywords

enantioselective Henry reaction / C₁-symmetric diamines / asymmetric reaction / nitroalkanol

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Acknowledgments

Generous financial support by the National Basic Research Program of China (973 Program: 2010CB833300) and the State Key Laboratory of Elemento-Organic Chemistry is gratefully acknowledged.

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg