Direct enantioselective C-acylation for the construction of a quaternary stereocenter catalyzed by a chiral bicyclic imidazole

Mo Wang; Xiao Zhang; Zheng Ling; Zhenfeng Zhang; Wanbin Zhang

doi:10.1039/c6cc09451a

Direct enantioselective C-acylation for the construction of a quaternary stereocenter catalyzed by a chiral bicyclic imidazole

Chem Commun (Camb). 2017 Jan 24;53(8):1381-1384. doi: 10.1039/c6cc09451a.

Authors

Mo Wang¹, Xiao Zhang¹, Zheng Ling¹, Zhenfeng Zhang², Wanbin Zhang³

Affiliations

¹ School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China. wanbin@sjtu.edu.cn.
² School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China. zhenfeng@sjtu.edu.cn.
³ School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China. wanbin@sjtu.edu.cn and School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China. zhenfeng@sjtu.edu.cn.

PMID: 28074967
DOI: 10.1039/c6cc09451a

Abstract

A direct enantioselective C-acylation of 3-substituted benzofuran-2(3H)-ones (with up to 97% ee) was developed using a chiral bicyclic imidazole catalyst OAc-DPI and an achiral tertiary amine additive DIPEA. The reaction mechanism for the direct C-acylation has been investigated using both experimental and theoretical studies.