(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. Foschi
Primo
;
D. Landini
Secondo
;
V. Mihali;A. Tagliabue
Ultimo
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.
Enantioselectivity; Prolines; Rearrangement; Sulfonamides
Settore CHIM/04 - Chimica Industriale
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/147397
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