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Diastereomerically and Enantiomerically Pure 2,3-Disubstituted Pyrrolidines from 2,3-Aziridin-1-ols Using a Sulfoxonium Ylide: A One-Carbon Homologative Relay Ring Expansion

Jennifer M. Schomaker, Somnath Bhattacharjee, Jun Yan and Babak Borhan*

*Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, Email:

J. M. Schomaker, S. Bhattacharjee, J. Yan, B. Borhan, J. Am. Chem. Soc., 2007, 129, 1996-2003.

DOI: 10.1021/ja065833p


The aza-Payne rearrangement of 2,3-aziridin-1-ols under basic conditions gives epoxy amines. Subsequent nucleophilic attack of the epoxide by dimethylsulfoxonium methylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.

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proposed mechanism

Key Words

Aza-Payne Rearrangement, Epoxides, Pyrrolidines

ID: J48-Y2007-0560