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

Authors

  • С. А. Вакаров I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Д. А. Груздев I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Е. Н. Чулаков I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Л. Ш. Садретдинова I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • М. А. Ежикова I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • М. И. Кодесс I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Г. Л. Левит I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • В. П. Краснов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1635

Keywords:

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

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

Author Biographies

С. А. Вакаров, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Сергей Анатольевич Вакаров

Д. А. Груздев, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Дмитрий Андреевич Груздев

Е. Н. Чулаков, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Евгений Николаевич Чулаков

Л. Ш. Садретдинова, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Лилия Ширмухаметовна Садретдинова

М. А. Ежикова, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Марина Александровна Ежикова

М. И. Кодесс, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Михаил Исаакович Кодесс

Г. Л. Левит, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Галина Львовна Левит

В. П. Краснов, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

Виктор Павлович Краснов

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Published

2014-07-05

Issue

No. 6 (2014)

Section

Original Papers