Brønsted acid catalyzed enantioselective α-amidoalkylation in the synthesis of isoindoloisoquinolines

The Journal of Organic Chemistry
Eider AranzamendiEsther Lete

Abstract

The Parham cyclization-intermolecular α-amidoalkylation sequence results in the facile enantioselective synthesis of 12b-substituted isoindoloisoquinolines (ee up to 95%) using BINOL-derived Brønsted acids. α-Amidoalkylation of indole occurs through the formation of a chiral conjugate base/bicyclic quaternary N-acyliminium ion pair.

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May 13, 2021·Organic & Biomolecular Chemistry·Nikola Topolovčan, Matija Gredičak

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