Ebolate additions to a chiral 3-hydroxypropionate 2,3-dication equivalent: enantioselective synthesis of beta, delta-dihydroxy esters

Optically active dicarbonyl cyclopentadienyliron(vinyl ether) BF4 salts were synthesized and utilized as chiral 3-hydroxypropionate 2,3-dication equivalents for the formation of beta, delta-dihydroxy esters. The synthetic strategy was characterized by the formation of of the diastereoisomers from the reaction of the starting material with (S)-propane-1,2-diols. The organometallic salts behaved as stabilized enantioselective carbocations toward carbon nucleophiles and mediated the formation of the desired esters via redox-promoted methoxycarbonylation.