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Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Wacker-Type Aerobic Oxidative Cyclization of Alkenes with tert-Butanesulfinamide Nucleophiles

Author:
Redford, Joanne E., McDonald, Richard I., Rigsby, Matthew L., Wiensch, Joshua D., Stahl, Shannon S.
Source:
Organic letters 2012 v.14 no.5 pp. 1242-1245
ISSN:
1523-7052
Subject:
Lewis bases, alkenes, chemical reactions, enantiomers, palladium, pyrrolidines, stereoselective synthesis
Abstract:
Palladium(II)-catalyzed aerobic oxidative cyclization of alkenes with tethered tert-butanesulfinamides furnishes enantiopure 2,5-disubstituted pyrrolidines, originating from readily available and easily diversified starting materials. These reactions are the first reported examples of metal-catalyzed addition of sulfinamide nucleophiles to alkenes.
Agid:
5784969