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Issue 13, 2015
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Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

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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

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Article information


Submitted
21 Nov 2014
Accepted
22 Dec 2014
First published
22 Dec 2014

Chem. Commun., 2015,51, 2690-2693
Article type
Communication

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

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