Organic Chemistry Portal



Stereospecific Consecutive Epoxide Ring Expansion with Dimethylsulfoxonium Methylide

Ekaterina D. Butova, Anastasiya V. Barabash, Anna A. Petrova, Christian M. Kleiner, Peter R. Schreiner and Andrey A. Fokin*

*Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, Email:

E. D. Butova, A. V. Barabash, A. A. Petrova, C. M. Kleiner, P. R. Schreiner, A. A. Fokin, J. Org. Chem., 2010, 75, 6229-6235.

DOI: 10.1021/jo101330p

see article for more reactions


Nucleophilic ring expansions of enantiomeric 2-mono- and 2,2-disubstituted epoxides and oxetanes with dimethylsulfoxonium methylide is a convenient general approach for a high-yielding preparation of optically active four- and five-membered cyclic ethers from oxiranes.

see article for more examples

Key Words

Oxetanes, Tetrahydrofurans

ID: J42-Y2010-2570