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A facile Zr-mediated multicomponent approach to arylated allylic alcohols and its application to the synthesis of highly substituted indenes and spiroindenes.

Authors
  • Guo, Shenghai
  • Liu, Yuanhong
Type
Published Article
Journal
Organic & biomolecular chemistry
Publication Date
Jun 21, 2008
Volume
6
Issue
12
Pages
2064–2070
Identifiers
DOI: 10.1039/b804888f
PMID: 18528567
Source
Medline
License
Unknown

Abstract

An efficient and one-pot procedure for the synthesis of arylated and stereodefined allylic alcohols has been achieved through zirconium-mediated multicomponent coupling reactions of alkynes, aldehydes (or ketones), and aryl iodides. The subsequent intramolecular Friedel-Crafts reactions of these allylic alcohols catalyzed by Brønsted or Lewis acids afford highly substituted indenes and spiroindenes under extremely mild reaction conditions. This methodology also provided a highly efficient route to the synthesis of spiroindenepiperidines.

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