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

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journal contribution
posted on 03.01.2008, 00:00 by Carlos Silva López, Carlos Pérez-Balado, Paula Rodríguez-Graña, Ángel R. de Lera
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.