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Molecular oxygen would be the most desirable oxidant in organic synthesis owing to its economically and environmentally favorable properties. Therefore, various methods have long been developed to utilize the molecular oxygen as the oxidizing reagent under mild reaction conditions. We also have reported a new oxygenation method on the olefin oxidation to corresponding alcohols, where atmospheric pressure of oxygen was involved as the oxidant along with (schiff-base)Mn(III) catalyst and sodium borohydride as the co-reagent. As a continuing effort in this field, we decided to examine the electron deficient olefins such as α,β-unsaturated esters as the reaction substrate. Direct hydroxylation of α,βunsaturated esters would provide the α-hydroxy esters, which comprise important functional groups frequently encountered in organic synthesis. Even though various preparative method on α-hydroxy esters has been reported, relatively few reports have been made utilizing molecular oxygen as the oxidant for the synthesis of α-hydroxy esters. In order to obtain the optimized reaction conditions in this study, we have examined some experimental parameters such as (schiff-base)Mn(III) complex, reaction solvent and reaction temperature. The optimized reaction condition was described in Table 1, where Mn(III) complex 1 (10 mol%) was employed as the catalyst under atmospheric pressure of oxygen along with two equivalents of sodium borohydride. The reaction was carried out using chloroform as a solvent at 0 C.

(Schiff-Base)Mn(III)-Catalyzed Hydroxylation of α,β-Unsaturated Esters Using Molecular Oxygen in the Presence of Metal Hydrides