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

CP Decicco, DJ Nelson, RL Corbett…

Index: Decicco, Carl P.; Nelson, David J.; Corbett, Ronald L.; Dreabit, Jason C. Journal of Organic Chemistry, 1995 , vol. 60, # 15 p. 4782 - 4785

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Citation Number: 17

Abstract

The addition of chiral imides to a-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 SN~ displacement of the triflate ...