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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
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摘要 Two new Cl-symmetric primary-secondary diamines were synthesized via the reaction of (S,S)-1,2- diphenyl ethylene diamine with 3,5-ditert-butyl salicylal- dehyde 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. Two new Cl-symmetric primary-secondary diamines were synthesized via the reaction of (S,S)-1,2- diphenyl ethylene diamine with 3,5-ditert-butyl salicylal- dehyde 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.
出处 《Frontiers of Chemical Science and Engineering》 SCIE EI CAS CSCD 2013年第4期408-414,共7页 化学科学与工程前沿(英文版)
关键词 enantioselective Henry reaction Cl-sym-metric diamines asymmetric reaction nitroalkanol enantioselective Henry reaction, Cl-sym-metric diamines, asymmetric reaction, nitroalkanol
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