The Direct Conversion of Esters to Ketones Enabled by a Traceless Activating Group

We report here the design and development of a method for the single-step conversion of esters to ketones with simple reagents. The selective transformation of esters to ketones, rather than tertiary alcohols, is made possible by the use of a transient sulfinate group on the nucleophile that activat...

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Bibliographic Details
Published in:Organic letters 2023-05, Vol.25 (17), p.3131-3135
Main Authors: Fier, Patrick S., Roberts, Riley A., Larson, Reed T.
Format: Article
Language:English
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Summary:We report here the design and development of a method for the single-step conversion of esters to ketones with simple reagents. The selective transformation of esters to ketones, rather than tertiary alcohols, is made possible by the use of a transient sulfinate group on the nucleophile that activates the adjacent carbon toward deprotonation to form a carbanion that adds to the ester, followed by a second deprotonation to prevent further addition. The resulting dianion undergoes spontaneous fragmentation of the SO2 group upon quenching with water to reveal the ketone product.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00992