Jump to main content
Jump to site search

Issue 9, 2017
Previous Article Next Article

Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives

Author affiliations

Abstract

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N′-dioxide–scandium(III) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.

Graphical abstract: Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Jun 2017, accepted on 20 Jul 2017 and first published on 24 Jul 2017


Article type: Edge Article
DOI: 10.1039/C7SC02809A
Citation: Chem. Sci., 2017,8, 6645-6649
  • Open access: Creative Commons BY license
  •   Request permissions

    Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives

    Y. Zhang, Y. Liao, X. Liu, X. Xu, L. Lin and X. Feng, Chem. Sci., 2017, 8, 6645
    DOI: 10.1039/C7SC02809A

    This article is licensed under a Creative Commons Attribution 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.

    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