UNNATURAL AMINO ACIDS. 2. SIMPLE METHOD OF OBTAINING ESTERS OF AZIRIDINE-2-CARBOXYLIC ACIDS BY A TRANSESTERIFICATION REACTION

Authors

  • B. Shtrumfs Latvian Institute of Organic Synthesis, Riga LV 1006
  • D. Chernyak Latvian Institute of Organic Synthesis, Riga LV 1006
  • I. Kums Latvian Institute of Organic Synthesis, Riga LV 1006
  • I. Kalvins Latvian Institute of Organic Synthesis, Riga LV 1006
  • P. Trapencieris Latvian Institute of Organic Synthesis, Riga LV 1006

Keywords:

diastereomers, esters of aziridine-2-carboxylic acid, enantiomers, transesterification

Abstract

A series of N-unsubstituted esters of aziridine-2-carboxylic acid has been obtained by transesterification in basic medium using primary, secondary, and tertiary alcohols. Methods of transesterification using various bases (K2CO3, ROLi, t-BuOK) have been compared. Transesterification with lithium alcoholates also affords the possibility of obtaining esters of N-substituted aziridine-2-carboxylic acids. Transesterification of chiral esters proceeds with retention of the configuration of the chiral center.

How to Cite
Shtrumfs, B.; Chernyak, D.; Kums, I.; Kalvins, I.; Trapencieris, P. Chem. Heterocycl. Compd. 2004, 40, 725. [Khim. Geterotsikl. Soedin. 2004, 850.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000040767.96090.cc

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Published

2004-06-25

Issue

No. 6 (2004)

Section

Original Papers