The Formation of a Crystalline Oxazolidin-5-one from (L)-Alanine and its Use as a Chiral Template in the Practical Synthesis of α-Substituted Alanine Esters

…, E Napolitano, J Xu, S Kapadia, D Byrne…

Index: Eriksson, Magnus; Napolitano, Elio; Xu, Jinghua; Kapadia, Suresh; Byrne, Denis; Nummy, Laurence; Grinberg, Nelu; Shen, Sherri; Lee, Heewon; Farina, Vittorio Chimia, 2006 , vol. 60, # 9 p. 566 - 573

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Citation Number: 4

Abstract

Three different protocols to synthesize oxazolidin-5-ones have been studied with the goal to develop a method to synthesize a diastereomerically pure oxazolidin-5-one. A novel method is reported that uses a dynamic crystallization-induced asymmetric transformation to isolate a single diastereomer of an oxazolidin-5-one in 92% yield on kilogram scale. Alkylation of the oxazolidin-5-one template leads to good-to-excellent yields of N-protected α- ...