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Enantioselective Rearrangement of Proline Sulfonamides: An Easy Entry to Enantiomerically Pure α‐Aryl Quaternary Prolines
Author(s) -
Foschi Francesca,
Landini Dario,
Lupi Vittoria,
Mihali Voichiţa,
Penso Michele,
Pilati Tullio,
Tagliabue Aaron
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000989
Subject(s) - enantiopure drug , enantioselective synthesis , chemistry , aryl , proline , stereochemistry , sulfonamide , combinatorial chemistry , ring (chemistry) , organic chemistry , amino acid , catalysis , biochemistry , alkyl
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 α‐aromatic prolines.