On the Reaction of Tryptophan Derivatives with N-Phenylselenyl
Phthalimide: The Nature of the Kinetic and Thermodynamic
Hexahydropyrrolo[2,3-b]indole Products. Alkylation of
Tryptophan with Inversion of Configuration
posted on 1999-08-18, 00:00authored byDavid Crich, Xianhai Huang
The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to
3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3-b]pyrroloindoles has been studied. It is established
that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple
protocol for the alkylation of tryptophan, leading to α-substituted tryptophans with clean inversion
of configuration, is presented.