SYNTHESIS OF NONRACEMIC 9-(1-METHOXYCARBONYLETHYL)-1,2,3,4-TETRAHYDROCARBAZOLE

Authors

  • А. В. Куркин Moscow M. V. Lomonosov State University, Moscow 119234
  • В. В. Нестеров Moscow M. V. Lomonosov State University, Moscow 119234
  • А. В. Карчава Moscow M. V. Lomonosov State University, Moscow 119234
  • М. А. Юровская Moscow M. V. Lomonosov State University, Moscow 119234

Keywords:

N-aryl-2,2,2-trichloroethylcarbamates, nonracemic 9-(1-methoxycarbonylethyl)-1,2,3,4-tetrahydrocarbazole, N-trifluoroacetyl-, N-benzenesulfonyl, N-tosylanilines, chiral N-alkyl-N-phenylhydrazine, (S)-lactic acid ethyl ester, Mitsunobu alkylation, desulfonylation, Fischer indolization, removal of activating groups

Abstract

A new approach has been proposed to the synthesis of indole derivatives containing a chiral substituent at the nitrogen atom, comprizing Fischer indolization of phenylhydrazines with a chiral substituent at the α-nitrogen atom. The initial hydrazines were obtained by the alkylation (Mitsunobu reaction applying optically active esters of lactic acid) of anilines containing an electron-accepting substituent at the amino group. Subsequent removal of the activating acceptor grouping was realized by nitrosation of the chiral secondary aniline followed by reduction of the corresponding N-nitroso compound.

How to Cite
Kurkin, A. V.; Nesterov, V. V.; Karchava, A. V.; Yurovskaya, M. A. Chem. Heterocycl. Compd. 2003, 39, 1466. [Khim. Geterotsikl. Soedin. 2003, 1665.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000014411.33252.d1

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Published

2003-11-25

Issue

No. 11 (2003)

Section

Original Papers