Asymmetric preparation of polysubstituted cyclopentanes by synergistic Pd(0)/amine catalyzed formal [3+2] cycloadditions of vinyl cyclopropanes with enals

We report herein a novel diastereo- and enantiocontrolled preparation of polysubstituted cyclopentanes by the formal [3+2] cycloadditions of vinyl cyclopropanes with enals. In constrast with previously developed strategies, our original approach is based on the synergistic merger of iminium/enamine...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (3), p.5332-5335
Main Authors: Laugeois, Maxime, Ponra, Sudipta, Ratovelomanana-Vidal, Virginie, Michelet, Véronique, Vitale, Maxime R
Format: Article
Language:English
Subjects:
Amines
Asymmetry
Catalysis
Cycloaddition
Organic compounds
Strategy
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Summary:We report herein a novel diastereo- and enantiocontrolled preparation of polysubstituted cyclopentanes by the formal [3+2] cycloadditions of vinyl cyclopropanes with enals. In constrast with previously developed strategies, our original approach is based on the synergistic merger of iminium/enamine organocatalysis with palladium(0) catalysis. The stereocontrolled [3+2] cycloaddition reaction of vinyl cyclopropanes with enals has been accomplished by merging organocatalysis with palladium(0) catalysis.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc01775d