162302-18-3Relevant academic research and scientific papers
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
Crich, David,Huang, Xianhai
, p. 7218 - 7223 (2007/10/03)
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.
