ASYMMETRIC-SYNTHESIS OF 2,3-DISUBSTITUTED SUCCINATES VIA CHIRAL OXAZOLIDINONE CONTROLLED DISPLACEMENT OF ALPHA-TRIFLUOROMETHANESULFONATE SUBSTITUTED ESTERS

The addition of chiral imides to alpha-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(N)2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.