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. 2015 Aug 19;137(32):10112-5.
doi: 10.1021/jacs.5b06390. Epub 2015 Aug 10.

Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals

Nicholas A White  1 , Tomislav Rovis  1
Affiliations

Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals

Nicholas A White et al. J Am Chem Soc. .

Erratum in

Abstract

An unprecedented N-heterocyclic carbene (NHC)-catalyzed annulation of enals to form 3,4-disubstituted cyclopentanones has been discovered. Aryl enals undergo dimerization in the presence of a single-electron oxidant to form C2 symmetric cyclopentanones. A cross-reaction has also been developed, allowing for the synthesis of differentially substituted cyclopentanones. Mechanistically, the reaction is thought to proceed through radical intermediates, further establishing the synthetic utility of this class of reactivity.

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Figures

Figure 1
Figure 1
Background
Scheme 1
Scheme 1
Proposed Catalytic Cycle
Scheme 2
Scheme 2
Control Experiments
Scheme 3
Scheme 3
Derivatization
See this image and copyright information in PMC

References

    1. For a review see: Flanigan DM, Michailidis-Romanov F, White NA, Rovis T. Chem. Rev. 2015;115 doi: 10.1021/acs.cev.5bhemr0060.

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