Synthesis of new carbohydrate-derived ketones as organocatalysts in the enantioselective epoxidation of arylalkenes. Part 2: Chiral ketones from sugars

A range of new, somewhat complex, stereochemically varied, and structurally related carbohydrate-derived ketones were synthesised by a simple method from the carbohydrate precursor (d-gluco and d-galacto derivatives). The common skeleton possesses the keto function sited on a seven-membered ring fused to positions 2 and 3 of the sugar moiety. Their chirality transfer capability in the dioxirane-mediated epoxidation of arylalkenes was evaluated.