Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives Via Intramolecular Pd-catalyzed Alkene Carboamination Reactions

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2014 Apr 15

PMID 24724560

Citations 3

Authors

Jeremiah Alicea

John P Wolfe

Affiliations

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Abstract

Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. The mechanism of these transformations is described, and a model that accounts for the observed product stereochemistry is proposed.

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