Journal
ORGANIC LETTERS
Volume 25, Issue 14, Pages 2504-2508Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00676
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Direct access to polyfluorinated lactams is achieved through Ca(NTf2)(2)-catalyzed reductive amination of biomass-derived keto acids with amines or amino acids with carbonyl derivatives under solvent-free conditions. The versatile protocols possess chemospecificity and good substrate tolerance, enabling the synthesis of five- to eight-membered lactams with diverse functionality and substitution patterns. The robustness of this methodology is demonstrated by its application in the late-stage functionalization of drug molecules.
Direct access to the polyfluorinated lactams through Ca(NTf2)(2) catalyzed by either the reductive amination of biomass-derived keto acids with amines or the reductive amination of amino acids with carbonyl derivatives under solvent-free conditions is realized. The two versatile protocols display chemospecificity and good substrate tolerance to deliver five- to eight-membered lactams with diverse functionality and substitution patterns. The robustness of the methodology is further demonstrated by subsequent application in the late-stage functionalization of drug molecules.
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