Radical Addition to the Carbonyl Carbon Promoted by Aqueous Titanium Trichloride: Stereoselective Synthesis of α,β-Dihydroxy Ketones

Article abstract of DOI:10.1021/jo00277a025

Ketyl radicals, formed by chemoselective Ti(III) reduction of α,β-dicarbonyl compounds, add to the carbonyl carbon of aldehydes under mild conditions to afford α,β-dihydroxy ketones in good to excellent yields.Simple diastereoselectivity strongly depends on the bulk of groups bonded to both the ketyl radical and the aldehydic function.The relative configuration of two the keto diols was established by single-crystal X-ray diffractometry.