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Issue 1, 2015
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Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes

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Abstract

Catalytic asymmetric desymmetrization represents an excellent strategy for accessing highly functionalized chiral building blocks. However, the application of desymmetrization for the synthesis of enantioenriched cyclopentane derivatives remained limited, when compared to chiral cyclohexanes. We have recently developed a desymmetrization protocol for prochiral 2,2-disubstituted cyclopentene-1,3-diones by direct catalytic asymmetric vinylogous nucleophilic addition of deconjugated butenolides. In this perspective, we give an overview of asymmetric desymmetrization reactions leading to enantioenriched cyclopentanes and their derivatives. The focus is kept confined to the diverse nature of reactions used for this purpose. A brief discussion on the potential future directions is also provided.

Graphical abstract: Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes

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Publication details

The article was received on 03 Aug 2014, accepted on 26 Sep 2014 and first published on 29 Sep 2014


Article type: Perspective
DOI: 10.1039/C4OB01649A
Citation: Org. Biomol. Chem., 2015,13, 18-24
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    Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes

    M. S. Manna and S. Mukherjee, Org. Biomol. Chem., 2015, 13, 18
    DOI: 10.1039/C4OB01649A

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