Mechanistic Insights into the Stereocontrolled Synthesis of Hexahydropyrrolo[2,3-b]indoles by Electrophilic Activation of Tryptophan Derivatives

Autor:	de Lera Ar, Carlos Silva López, Carlos Pérez-Balado, Rodríguez-Graña P
Rok vydání:	2007
Předmět:	Indoles Molecular Structure Stereochemistry Chemistry Organic Chemistry Tryptophan Stereoisomerism Biochemistry Hydrocarbons Brominated Cyclization Electrophile Pyrroles Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 10:77-80
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol702732j
Popis:	A three-step mechanism involving the formation and rearrangement of an intermediate with indoline-azetidine spirocyclic core structure was shown by DFT computations to account for the electrophilic cyclization of tryptophan derivatives to hexahydropyrrolo[2,3-b]indoles. The corresponding 3a-bromo derivatives have been obtained in high yields and synthetically useful exo/endo ratios.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6bd7484b9d1d837f736993f86ec35d86 https://doi.org/10.1021/ol702732j Zobrazit plný text záznamu