Enantioselective Rearrangement of Proline Sulfonamides: An Easy Entry to Enantiomerically Pure α-Aryl Quaternary Prolines

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 (E...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-09, Vol.16 (35), p.10667-10670
Main Authors: Foschi, Francesca, Landini, Dario, Lupi, Vittoria, Mihali, Voichiţa, Penso, Michele, Pilati, Tullio, Tagliabue, Aaron
Format: Article
Language:English
Subjects:
Aromatic compounds
enantioselectivity
Esters
Molecular Structure
Proline
Proline - chemistry
prolines
rearrangement
Stereoisomerism
sulfonamides
Sulfonamides - chemistry
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201000989