Highly Enantioselective Synthesis of Acyclic N, N'-Acetals by Chiral Urea Derived from Quinine Catalyzed the Addition of Aryl Amines to Isatin-Derived Ketimines

Yuxin Liu; Jingdong Wang; Zhonglin Wei; Jungang Cao; Dapeng Liang; Yingjie Lin; Haifeng Duan

doi:10.1021/acs.orglett.9b02098

Highly Enantioselective Synthesis of Acyclic N, N'-Acetals by Chiral Urea Derived from Quinine Catalyzed the Addition of Aryl Amines to Isatin-Derived Ketimines

Org Lett. 2019 Jul 19;21(14):5719-5724. doi: 10.1021/acs.orglett.9b02098. Epub 2019 Jul 2.

Authors

Yuxin Liu¹, Jingdong Wang¹, Zhonglin Wei¹, Jungang Cao¹, Dapeng Liang¹, Yingjie Lin¹, Haifeng Duan¹

Affiliation

¹ Department of Organic Chemistry, College of Chemistry , Jilin University , 2699 Qianjin Street , Changchun 130012 , China.

PMID: 31265315
DOI: 10.1021/acs.orglett.9b02098

Abstract

N,N'-Acetals are sensitive compounds, and the challenging asymmetric synthesis of acyclic N,N'-acetals by the general addition of amines to ketimines has never been reported so far. In this study, highly enantioselective addition of aryl amines to isatin-derived ketimines catalyzed by chiral urea derived from quinine was developed. A series of new acyclic N,N'-acetals were constructed by this protocol in high to excellent yields (78-99%) and high to excellent enantioselectivities (76-96% ee).

Publication types

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