(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.
Enantioselective rearrangement of proline sulfonamides: an easy entry to enantiomerically pure α-aryl quaternary prolines / F. Foschi, D. Landini, V. Lupi, V. Mihali, M. Penso, T. Pilati, A. Tagliabue. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 16:35(2010), pp. 10667-10670. [10.1002/chem.201000989]
Enantioselective rearrangement of proline sulfonamides: an easy entry to enantiomerically pure α-aryl quaternary prolines
F. FoschiPrimo
;D. LandiniSecondo
;V. Mihali;A. TagliabueUltimo
2010
Abstract
(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.
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