4.7 Article

Catalytic direct-type substitution reaction of alpha-alkyl enolates: a Pd/Bronsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates

Journal

CHEMICAL COMMUNICATIONS
Volume -, Issue 47, Pages 6354-6356

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b815845b

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Funding

  1. Japan Society of the Promotion of Science (JSPS)

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A mild and efficient process for the direct-type catalytic allylation of sulfonylimidates has been developed; this reaction represents the first example of Bronsted base-catalysed, in situ generation and use of alpha-alkyl enolates in substitution reactions; the success of this methodology stems from the tunable alpha-proton acidity and nucleophilicity of sulfonylimidates, which could be harnessed in the realization of a broader range of catalytic direct-type reactions using ester equivalents as nucleophiles.

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