Jump to main content
Jump to site search

Issue 12, 2016
Previous Article Next Article

Non-bonding 1,5-S⋯O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles

Author affiliations

Abstract

Isothiourea-catalyzed annulations between 2-acyl benzazoles and α,β-unsaturated acyl ammonium intermediates are selectively tuned to form either lactam or lactone heterocycles in good yields (up to 95%) and high ee (up to 99%) using benzothiazole or benzoxazole derivatives, respectively. Computation gives insight into the significant role of two 1,5-S⋯O interactions in controlling the structural preorganization and chemoselectivity observed within the lactam synthesis with benzothiazoles as nucleophiles. When using benzazoles the absence of a second stabilizing non-bonding 1,5-S⋯O interaction leads to a dominant C–H⋯O interaction in determining structural preorganization and lactone formation.

Graphical abstract: Non-bonding 1,5-S⋯O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles

Back to tab navigation

Supplementary files

Publication details

The article was received on 29 Feb 2016, accepted on 02 Jul 2016 and first published on 04 Jul 2016


Article type: Edge Article
DOI: 10.1039/C6SC00940A
Citation: Chem. Sci., 2016,7, 6919-6927
  • Open access: Creative Commons BY license
  •   Request permissions

    Non-bonding 1,5-S⋯O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles

    E. R. T. Robinson, D. M. Walden, C. Fallan, M. D. Greenhalgh, P. H. Cheong and A. D. Smith, Chem. Sci., 2016, 7, 6919
    DOI: 10.1039/C6SC00940A

    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