Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of α-Trifluoromethanesulfonate Substituted Esters

Article abstract of DOI:10.1021/jo00120a022

The addition of chiral imides to α-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields.Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products.The reactions proceed through the predicted S_N2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.