title: Lewis acid catalyzed carbon-carbon bond cleavage of aryl oxiranyl diketones: synthesis of cis-2,5-disubstituted 1,3-dioxolanes.
abstract: Carbonyl ylide is one of the most important intermediates which can undergo a series of 1,3-dipolar cycloaddition reactions. The C-C heterolysis of oxirane is believed to be the most atom-economic and straightforward way to generate carbonyl ylide. However, this chemistry was only achieved under photochemical and thermal conditions in past years. In this work, the one-step diastereoselective synthesis of cis-2,5-disubstituted 1,3-dioxolanes via [3 + 2] cycloadditions of aldehydes and carbonyl ylide, which is obtained from Lewis acid catalyzed C-C bond heterolysis of aryl oxiranyl diketones at ambient temperature, is described.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai, PR China.
authors.forename: Zuliang
authors.initials: Z
authors.lastname: Chen
authors.forename: Lai
authors.initials: L
authors.lastname: Wei
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhang