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

Joanne E. Redford, Richard I. McDonald, Matthew L. Rigsby, Joshua D. Wiensch, Shannon S. Stahl

Organic Letters · 2012 · 48 citations · 47 references

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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.

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