Access to Chiral 1-Aminoindene Derivatives by Asymmetric Brønsted Acid Catalysis

Abstract

Asymmetric organocatalysis is emerging as an elegant tool for accelerating chemical reactions and creating specific types of molecules. Chiral Brønsted acid catalysis is an important area of organocatalysis. We recently described an intramolecular iminium-ion cyclization reaction of 2-alkenylbenzaldimines catalyzed by a chiral Brønsted acid (a BINOL-derived N-triflylphosphoramide) for the synthesis of chiral 1-aminoindenes and tetracyclic 1-aminoindanes in good yields and high enantioselectivities. One of the resulting 1-aminoindenes is a useful intermediate for the synthesis of (S)-rasagiline, an effective drug for the symptomatic treatment of Parkinson’s disease. Moreover, some tetracyclic 1-aminoindanes are present in the skeletons of homoisoflavanoid natural products such as brazilin.

Key words

asymmetric catalysis - organocatalysis - Brønsted acid catalysis - iminium ions - aminoindenes - aminoindanes

Publication History

Received: 10 November 2021

Accepted after revision: 24 November 2021

Accepted Manuscript online:
24 November 2021

Article published online:
21 December 2021

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