Open Access Open Access  Restricted Access Subscription Access

DIASTEREOSELECTIVE ACYLATION OF RACEMIC HETEROCYCLIC AMINES WITH N-TOSYL-(S)-PROLYL CHLORIDE AND ITS STRUCTURAL ANALOGS

С. А. Вакаров, Д. А. Груздев, Е. Н. Чулаков, Л. Ш. Садретдинова, М. А. Ежикова, М. И. Кодесс, Г. Л. Левит, В. П. Краснов
Cover Image

Abstract


A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.

How to Cite
Vakarov, S. A.; Gruzdev, D. A.; Chulakov, E. N.; Sadretdinova, L. Sh.; Ezhikova, M. A.; Kodess, M. I.; Levit, G. L.; Krasnov, V. P. Chem. Heterocycl. Compd. 2014, 50, 838. [Khim. Geterotsikl. Soedin. 2014, 908.]

For this article in the English edition see DOI 10.1007/s10593-014-1538-8


Keywords


acyl chlorides; proline; racemic amines; acylation; diastereoselectivity; kinetic resolution

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv