1254718-89-2Relevant academic research and scientific papers
Enantioselective rearrangement of proline sulfonamides: An easy entry to enantiomerically pure α-aryl quaternary prolines
Foschi, Francesca,Landini, Dario,Lupi, Vittoria,Mihali, Voichita,Penso, Michele,Pilati, Tullio,Tagliabue, Aaron
supporting information; experimental part, p. 10667 - 10670 (2010/11/16)
(Figure Presented) Enantiopure quaternary prolines have been prepared by stereoselective rearrangement of N-(arylsulfonyl)proline tert-butyl esters under basic conditions (see scheme), without any external source of stereochemical information. The sulfonamide aromatic ring must contain an electron-withdrawing group (EWG), which stabilizes an intermediate Meisenheimer complex. The overall process provides easy entry to a series of optically pure a-aromatic prolines.
