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

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 NaBH 4 . The combination of the ligand from 3,5-ditert-butyl salicylaldehyd...

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Bibliographic Details
Published inFrontiers of chemical science and engineering Vol. 7; no. 4; pp. 408 - 414
Main Authors Zhang, Lili, Liu, Ming, Ma, Shijun, Huang, Yaodong, Wang, Yongmei
Format Journal Article
LanguageEnglish
Published Berlin/Heidelberg Springer Berlin Heidelberg 01.12.2013
Subjects
Chemistry
Chemistry and Materials Science
Industrial Chemistry/Chemical Engineering
Nanotechnology
Research Article
asymmetric reaction
nitroalkanol
enantioselective Henry reaction
symmetric diamines
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Summary: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 NaBH 4 . 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.
ISSN:2095-0179
2095-0187
DOI:10.1007/s11705-013-1343-4