Jump to main content
Jump to site search

Issue 8, 2015
Previous Article Next Article

Rh-catalyzed desymmetrization of α-quaternary centers by isomerization-hydroacylation

Author affiliations

Abstract

We describe a Rh-catalyzed desymmetrization of all-carbon quaternary centers from α,α-bis(allyl)aldehydes by a cascade featuring isomerization and hydroacylation. This desymmetrization competes with two other novel olefin functionalizations that are triggered by C–H bond activation, including carboacylation and bisacylation. A BIPHEP ligand promotes enantioselective formation of α-vinylcyclopentanones. Mechanistic studies support irreversible and enantioselective olefin-isomerization followed by olefin-hydroacylation.

Graphical abstract: Rh-catalyzed desymmetrization of α-quaternary centers by isomerization-hydroacylation

Back to tab navigation

Supplementary files

Article information


Submitted
29 Apr 2015
Accepted
29 May 2015
First published
12 Jun 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 4479-4483
Article type
Edge Article

Rh-catalyzed desymmetrization of α-quaternary centers by isomerization-hydroacylation

J. Park, K. G. M. Kou, D. K. Kim and V. M. Dong, Chem. Sci., 2015, 6, 4479
DOI: 10.1039/C5SC01553G

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.


Social activity

Search articles by author

Spotlight

Advertisements