Jump to main content
Jump to site search

Issue 2, 2016
Previous Article Next Article

Rh(III)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

Author affiliations

Abstract

The Rh(III)-catalyzed cascade addition of a C–H bond across alkene and carbonyl π-bonds is reported. The reaction proceeds under mild reaction conditions with low catalyst loading. A range of directing groups were shown to be effective as was the functionalization of alkenyl in addition to aromatic C(sp2)–H bonds. When the enone and aldehyde electrophile were tethered together, cyclic β-hydroxy ketones with three contiguous stereocenters were obtained with high diastereoselectivity. The intermolecular three-component cascade reaction was demonstrated for both aldehyde and imine electrophiles. Moreover, the first X-ray structure of a cationic Cp*Rh(III) enolate with interatomic distances consistent with an η3-bound enolate is reported.

Graphical abstract: Rh(iii)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

Back to tab navigation

Supplementary files

Publication details

The article was received on 31 Oct 2015, accepted on 23 Nov 2015 and first published on 01 Dec 2015


Article type: Edge Article
DOI: 10.1039/C5SC04138D
Citation: Chem. Sci., 2016,7, 1474-1479
  • Open access: Creative Commons BY license
  •   Request permissions

    Rh(III)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

    J. A. Boerth and J. A. Ellman, Chem. Sci., 2016, 7, 1474
    DOI: 10.1039/C5SC04138D

    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