CHIRALLY N-SUBSTITUTED INDOLE-2-CARBALDEHYDES. PREPARATION AND USE IN ASYMMETRIC SYNTHESIS

Authors

  • Н. Е. Голанцов M. V. Lomonosov State University, Moscow 119234
  • А. В. Карчава M. V. Lomonosov State University, Moscow 119234
  • З. А. Старикова A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow 119991
  • Ф. М. Долгушин A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow 119991
  • М. А. Юровская M. V. Lomonosov State University, Moscow 119234

DOI:

https://doi.org/10.1007/8170

Keywords:

N-substituted indoles, chiral aldehydes, 2-cyanoindole, aza Diels–Alder reaction, asymmetric synthesis, Mitsunobu reaction

Abstract

A simple method is proposed for the synthesis of optically active indole-2-carbaldehydes via alkylation of 2-cyanoindole by optically active secondary alcohols and subsequent reduction of the cyano group to an aldehyde. Reaction of the aldehydes obtained with aromatic amines gave imines whose reaction with the Danishefsky diene was studied.  The structure of the major diastereomer of (2R')-1-phenyl-2-[1-((1R')-1-phenylethyl)indol-2-yl]-1,2,3,4-tetrahydropyridine-4-one and minor  diastereomer  (2S)-2-[1-((1S)-2-methoxy-1-phenylethyl)indol-2-yl]-1-phenyl-1,2,3,4-tetrahydropyridine-4-one respectively  were established by X-ray analysis.

How to Cite
Golantsov, N. E.; Karchava, A. V.; Starikova, Z. A.; Dolgushin, F. M.; Yurovskaya, M. A.  Chem. Heterocycl. Compd. 2005, 41, 1290. [Khim. Geterotsikl. Soedin. 2005, 1540.]

For this article in the English edition, see DOI 10.1007/s10593-005-0315-0


Downloads

Published

2023-10-19

Issue

No. 10 (2005)

Section

Original Papers