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

Authors

  • Magnus Eriksson
  • Elio Napolitano
  • Jinghua Xu
  • Suresh Kapadia
  • Denis Byrne
  • Laurence Nummy
  • Nelu Grinberg
  • Sherri Shen
  • Heewon Lee
  • Vittorio Farina

DOI:

https://doi.org/10.2533/chimia.2006.566

Keywords:

Crystallization-induced asymmetric transformation, Diastereoselective alkylation, Alpha,alpha'-disubstituted amino acid, Oxazolidin-5-one

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-substituted alanine esters in >98–99% ee.

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Published

2006-09-27

Issue

Section

Scientific Articles

How to Cite

[1]
M. Eriksson, E. Napolitano, J. Xu, S. Kapadia, D. Byrne, L. Nummy, N. Grinberg, S. Shen, H. Lee, V. Farina, Chimia 2006, 60, 566, DOI: 10.2533/chimia.2006.566.