Download PDF
Synthesis 1989; 1989(8): 622-623
DOI: 10.1055/s-1989-27337
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

An Efficient Synthesis of (4S)-(-)-4-Isopropyl-2-oxazolidinone

Peter G. M. Wuts* , Lynn E. Pruitt
  • *Chemical Process Research and Development, The Upjohn Co., 1500-230-4, Kalamazoo, MI 49001, USA
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A new, efficient, cost-effective method for the preparation of the Evans' chiral auxiliary (4S)-4-isopropyl-2-oxazolidinone (4) is described. A Schotten-Baumann acylation of valine with phenyl carbonochloridate quantitatively affords the protected valine, which is then reduced with borane in tetrahydrofuran to give an alcohol. Cyclization with a catalytic amount, of potassium tert-butoxide gives 4 in 81% overall yield and in 41-43% after crystallization from ethyl acetate/n-hexane.