Jump to main content
Jump to site search

Issue 7, 2015
Previous Article Next Article

Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans

Author affiliations

Abstract

Disclosed herein is a stereoselective method for the synthesis of 2,3-furan fused carbocycles bearing adjacent quaternary and tertiary carbon stereocenters. The chemistry is based on an asymmetric addition of β-ketoesters to 2-(1-alkynyl)-2-alkene-1-ones catalysed by natural cinchona alkaloids followed by a silver-catalysed intramolecular cycloisomerisation. By exploiting the distinct catalysis modes of quinine, which can act either as a general base or, upon opportune modifications, as a phase transfer catalyst, a complete switch of the enforced sense of diastereoinduction is achieved. The stereodivergent systems enable access to the full matrix of all possible stereoisomeric products.

Graphical abstract: Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans

Back to tab navigation

Supplementary files

Publication details

The article was received on 23 Mar 2015, accepted on 25 Apr 2015 and first published on 27 Apr 2015


Article type: Edge Article
DOI: 10.1039/C5SC01052G
Author version
available:
Download author version (PDF)
Chem. Sci., 2015,6, 4242-4246
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans

    C. Verrier and P. Melchiorre, Chem. Sci., 2015, 6, 4242
    DOI: 10.1039/C5SC01052G

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements