title: L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: effects of the side amide group on catalytic performances.
abstract: A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure-efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and non-arylamido-type catalyst 6c exhibited high reactivity and enantioselectivity, furnishing the reduction of a wide variety of N-aryl imines with high isolated yields (up to 98%) and ee values (up to 96%) under mild conditions. Moreover, these two catalysts complement each other in terms of their tolerances to nonaromatic ketimines and non-methyl ketimines.
authors.affiliation: Department of Pharmaceutics Engineering, Xihua University, Chengdu, China. zhouyuwang77@gmail.com
authors.forename: Zhouyu
authors.initials: Z
authors.lastname: Wang
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.forename: Li
authors.initials: L
authors.lastname: Zhou
authors.forename: Jian
authors.initials: J
authors.lastname: Sun
mesh_terms: D002384:Catalysis; D005559:Formamides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry*; D010875:Pipecolic Acids / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
chemical_list: D005559:Formamides; D007097:Imines; D058115:Lewis Bases; D010875:Pipecolic Acids; D012821:Silanes; C065893:trichlorosilane