Factors governing the ratio of isomeric oxabicyclo[3.2.1]octanones formed on Baeyer–Villiger oxidation of some 5-endo,7-anti-disubstituted bicyclo[2.2.1]heptan-2-ones

Abstract

It was found that the outcome of Baeyer–Villiger oxidation of 5-endo,7-anti-disubstituted bicyclo[2.2.1]heptan-2-ones was influenced by at least three factors: (i) the electronegativity of the substituent at C-7; (ii) the hydrogen-bonding capability of the substituent at C-5; and (iii) the peracid employed. The optimum substituents and reaction conditions for oxidation of a bicycloheptanone to the corresponding 2-oxabicyclo[3.2.1]octan-3-one were delineated and used in the synthesis of a prostaglandin intermediate.