Jump to main content
Jump to site search

Issue 13, 2015
Previous Article Next Article

Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

Author affiliations

Abstract

An unusual room temperature β-lactone decarboxylation facilitated a five-step enantioselective formal synthesis of the cyclopentane core of an estrogen receptor β-agonist. A computational study probed the underlying factors facilitating unprecedented, rapid decarboxylation. Aryl substitution promotes faster reaction in the retro-[2+2] as a result of conjugative stabilization with the forming olefin. Additionally, the configuration of the α-ester in these fused β-lactones leads to differential decarboxylation rates.

Graphical abstract: Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Nov 2014, accepted on 22 Dec 2014 and first published on 22 Dec 2014


Article type: Communication
DOI: 10.1039/C4CC09308A
Citation: Chem. Commun., 2015,51, 2690-2693
  •   Request permissions

    Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

    D. T. Cohen, R. C. Johnston, N. T. Rosson, P. H. Cheong and K. A. Scheidt, Chem. Commun., 2015, 51, 2690
    DOI: 10.1039/C4CC09308A

Search articles by author

Spotlight

Advertisements