Enantioselective synthesis of 1-aminoindene derivatives via asymmetric Brønsted acid catalysis

Xiang Wu; Du Ding; Ying Zhang; Hua-Jie Jiang; Tao Wang; Li-Ping Zhao

doi:10.1039/d1cc03568a

Enantioselective synthesis of 1-aminoindene derivatives via asymmetric Brønsted acid catalysis

Chem Commun (Camb). 2021 Sep 23;57(76):9680-9683. doi: 10.1039/d1cc03568a.

Authors

Xiang Wu^{1

2}, Du Ding³, Ying Zhang³, Hua-Jie Jiang³, Tao Wang¹, Li-Ping Zhao¹

Affiliations

¹ Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei 230009, China. wuxiang@hfut.edu.cn.
² Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.
³ Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

PMID: 34486623
DOI: 10.1039/d1cc03568a

Abstract

We describe a catalytic asymmetric iminium ion cyclization reaction of simple 2-alkenylbenzaldimines using a BINOL-derived chiral N-triflyl phosphoramide. The corresponding 1-aminoindenes and tetracyclic 1-aminoindanes are formed in good yields and high enantioselectivities. Further, the chemical utility of the obtained enantiopure 1-aminoindene is demonstrated for the asymmetric synthesis of (S)-rasagiline.