A Facile Method for the Synthesis of Polycyclic Indole Derivatives:  The Generation and Reaction of Tungsten-Containing Azomethine Ylides

Treatment of N-(o-alkynylphenyl)imine derivatives with W(CO)5(L) induces the 5-endo-mode of cyclization of the imine nitrogen onto the electrophilically activated alkyne moiety to afford a novel reactive species, a metal-containing azomethine ylide. [3 + 2] cycloaddition of this ylide species with v...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2002-10, Vol.124 (39), p.11592-11593
Main Authors: Kusama, Hiroyuki, Takaya, Jun, Iwasawa, Nobuharu
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Treatment of N-(o-alkynylphenyl)imine derivatives with W(CO)5(L) induces the 5-endo-mode of cyclization of the imine nitrogen onto the electrophilically activated alkyne moiety to afford a novel reactive species, a metal-containing azomethine ylide. [3 + 2] cycloaddition of this ylide species with various electron-rich alkenes proceeds smoothly to give unstable carbene complexes, which in turn undergo 1,2-hydrogen-, alkyl-, and aryl-migration to afford in good yield 6-5-5 tricyclic indole skeletons having an alkyl or an aryl substituent at the 3-position of the indole nucleus.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja027589h