Concerted 1,2-Carbonyl Migration in Organic Synthesis. A Practical Synthesis of Spiro Cyclic 1,3-Diketones

Article abstract of DOI:10.1021/jo00225a105

A general method for the synthesis of α,β-unsaturated cyclic enones is described that involves the α-thioalkylation of cyclic silyl enol ethers in tandem with a low-temperature metaperiodate oxidative dehydrosulfenylation of β-keto sulfoxide.The facile Lewis acid catalyzed acyl migration of a series of α,β-epoxy ketones affords a practical synthesis of cyclic spiro 1,3-diketones.