The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and rearomatization.

Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

MARI, MICHELE;LUCARINI, SIMONE;BARTOCCINI, FRANCESCA;PIERSANTI, GIOVANNI;SPADONI, GILBERTO
2014-01-01

Abstract

The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and rearomatization.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2601583
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