Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives

Yong Xia; Lili Lin; Fenzhen Chang; Yuting Liao; Xiaohua Liu; Xiaoming Feng

doi:10.1002/anie.201604735

Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives

Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12228-32. doi: 10.1002/anie.201604735. Epub 2016 Jul 4.

Authors

Yong Xia¹, Lili Lin¹, Fenzhen Chang¹, Yuting Liao¹, Xiaohua Liu², Xiaoming Feng^{3

4}

Affiliations

¹ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
² Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China. liuxh@scu.edu.cn.
³ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China. xmfeng@scu.edu.cn.
⁴ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China. xmfeng@scu.edu.cn.

PMID: 27376785
DOI: 10.1002/anie.201604735

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.

Keywords: asymmetric catalysis; enantioselectivity; heterocycles; scandium; small ring systems.

Publication types

Research Support, Non-U.S. Gov't