Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides.

Author(s) Guissart, C.; Barros, A.; Barata, L.Rosa; Evano, G.
Journal Org Lett
Date Published 2018 09 07

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N, O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.

DOI 10.1021/acs.orglett.8b01896
ISSN 1523-7052
Citation Org Lett. 2018;20(17):50985102.

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