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Issue 51, 2017
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Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis

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Abstract

Highly diastereo and enantioselective [4+2] cycloadditions have been achieved between pyrrolidone-derived cyclic enones and α-haloaldehydes under mild conditions. Relying on extremely reactive in-situ generated chiral N-heterocyclic carbenes, this stereoselective annulation proceeds efficiently even on the gram scale with the catalyst loading as low as 0.025 mol% (250 ppm). A variety of cis-substituted bicyclic dihydropyranones can be produced in up to 96% yield with up to >99% ee. In addition, simple, inexpensive linear aldehydes such as n-propanal can be used directly in asymmetric cycloadditions via oxidative N-heterocyclic carbene organocatalysis with low catalyst loading. This method may provide an economical and practical approach for the asymmetric synthesis of medicinally relevant molecules.

Graphical abstract: Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis

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Publication details

The article was received on 16 Apr 2017, accepted on 05 Jun 2017 and first published on 05 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC02921G
Citation: Chem. Commun., 2017,53, 6875-6878
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    Highly enantioselective synthesis of fused bicyclic dihydropyranones via low-loading N-heterocyclic carbene organocatalysis

    J. Li, L. Fu, J. Wu, K. Yang, Q. Li, X. Gou, C. Peng, B. Han and X. Shen, Chem. Commun., 2017, 53, 6875
    DOI: 10.1039/C7CC02921G

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