Mechanistic insights into the stereocontrolled synthesis of hexahydropyrrolo[2,3-b]indoles by electrophilic activation of tryptophan derivatives.
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.
López
Carlos Silva
CS
Departamento de Química OrgAnica, Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain.
Pérez-Balado
Carlos
C
Rodríguez-Graña
Paula
P
de Lera
Angel R
AR
D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D006842:Hydrocarbons, Brominated; D007211:Indoles; D011758:Pyrroles; D014364:Tryptophan