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

CÚline Guissart, Andre Barros, Luis Rosa Barata, Gwilherm Evano*

*Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, UniversitÚ libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium, Email: gevanoulb.ac.be

C. Guissart, A. Barros, L. R. Barata, G. Evano, Org. Lett., 2018, 20, 5090-5093.

DOI: 10.1021/acs.orglett.8b01896 (free Supporting Information)


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Abstract

A catalytic amount of ytterbium(III) triflate as a Lewis acid promoter enables the conversion of a broad range of imides in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields.

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Application of Ytterbium-Catalyzed Amidation of Imides to Evans’ Alkylation and Aldolization Products



Key Words

esterification, hydrolysis


ID: J54-Y2018