Dimethyldioxirane epoxidation of alkenes bearing two electron donating substituents

Article abstract of DOI:10.1016/S0040-4039(00)79649-3

Various enol-type alkenes, such as 2,3-dimethylbenzodioxin (1), O-tetrabenzyl glycal (3), 1,2-bis(trimethylsilyloxy)cycloalkenes (9) were transformed in excellent yields to their labile epoxides by dimethyldioxirane (as acetone solution); the silyl ketene acetal 5 and 2-methyl-3-trimethylsilyloxybenzo[b]furan (7) gave the corresponding epoxide rearrangement products.