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Efficient Direct Synthesis of Aziridine‐Containing Chiral Tridentate Ligands by the Iminium‐Mediated Self‐Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes
Author(s) -
Chen Xingpeng,
Lin Chao,
Du Hongguang,
Xu Jiaxi
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801545
Subject(s) - enantiopure drug , aziridine , chemistry , iminium , trifluoromethanesulfonate , aldol reaction , azide , imine , ring (chemistry) , combinatorial chemistry , stereoselectivity , enantioselective synthesis , organic chemistry , stereochemistry , catalysis
An efficient method for the direct synthesis of aziridine‐containing chiral tridentate ligands was developed from enantiopure aziridines and salicylaldehydes. The method achieved the regiospecific cleavage of more substituted C−N bonds of aziridines through an iminium‐mediated self‐ring opening reaction of aziridines with up to 95% yield and complete inversion of configuration. The ( S )‐2‐alkylaziridine‐derived tridentate ligands displayed excellent activity and stereoselectivity in the zinc trifluoromethanesulfonate‐catalyzed asymmetric aldol reactions of acetone and aromatic aldehydes.