The first organocatalytic addition of 2-trimethylsilyloxyfuran to carbonyl compounds: hydrogen-bond catalysis in γ-butenolides synthesis

This letter describes the first example of diastereoselective ‘organocatalyzed’ synthesis of the butenolide products substituted at the γ-position by a chain bearing hydroxyl groups. The urea-derivative 4 has proved to be an efficient catalyst for the addition of the commercial TMSOF to carbonyl compounds under solvent-free conditions. The reaction conditions and generality of the procedure have been examined.