Jump to main content
Jump to site search


Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation

Author affiliations

Abstract

We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.

Graphical abstract: Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Aug 2019, accepted on 26 Aug 2019 and first published on 27 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03832A
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

  •   Request permissions

    Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation

    V. Lanke, F. Zhang, A. Kaushansky and I. Marek, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03832A

    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