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


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.

SUBMITTER: Mari M 

PROVIDER: S-EPMC4168769 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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

Mari Michele M   Lucarini Simone S   Bartoccini Francesca F   Piersanti Giovanni G   Spadoni Gilberto G  

Beilstein journal of organic chemistry 20140826


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. ...[more]

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