Ozonolysis of Morita-Baylis-Hillman Adducts Originated from Aromatic Aldehydes: An Expeditious Diastereoselective Approach for the Preparation of α,β-Dihydroxy-esters.

Abstract We disclose herein ozonolysis of Morita–Baylis–Hillman adducts originated from aromatic aldehydes. This efficient reaction provides α-ketoesters with different substitution patterns on the aromatic ring. Diastereoselective reduction of the corresponding α-ketoester obtained in the oxidative cleavage step provides α,β-dihydroxy-esters with excellent degree of anti diastereoselection. The method is simple and easy to execute and is therefore a valuable alternative to prepare either α-ketoesters or α,β-dihydroxy-esters.