title: Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives.
abstract: A highly efficient asymmetric ring-opening/cyclization/retro-Mannich reaction of cyclopropyl ketones with aryl 1,2-diamines has been realized using a chiral N,N'-dioxide/Sc(III) catalyst. Benzimidazoles containing chiral side chains were generated under mild reaction conditions in excellent outcomes (up to 99 % yield and 97 % ee). This method also provides efficient access to chiral benzimidazole-substituted amide and cycloheptene derivatives.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Xia
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
authors.forename: Fenzhen
authors.initials: F
authors.lastname: Chang
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
authors.forename: Yuting
authors.initials: Y
authors.lastname: Liao
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China. liuxh@scu.edu.cn.
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China. xmfeng@scu.edu.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China. xmfeng@scu.edu.cn.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
keywords: asymmetric catalysis; enantioselectivity; heterocycles; scandium; small ring systems