Issue 76, 2021

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Jūl. 2021
Accepted
24 Aug. 2021
First published
24 Aug. 2021

Chem. Commun., 2021,57, 9680-9683

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

X. Wu, D. Ding, Y. Zhang, H. Jiang, T. Wang and L. Zhao, Chem. Commun., 2021, 57, 9680 DOI: 10.1039/D1CC03568A

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