LiNTf2-Catalyzed Aminolysis of Lactones with Stoichiometric Quantities of Amines

Claudia Lalli, Andrea Trabocchi, Gloria Menchi, Antonio Guarna*

*Dipartimento di Chimica Organica ‘Ugo Schiff', Università degli Studi di Firenze, Polo Scientifico e Tecnologico, Via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy, Email: antonio.guarnaunifi.it

C. Lalli, A. Trabocchi, G. Menchi, A. Guarna, Synlett, 2008, 189-192.

DOI: 10.1055/s-2007-1000882

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Abstract

LiNTf₂ is able to activate cyclic esters towards ring opening with a stoichiometric amount of amines, thus leading to clean open-chain amides under mild conditions. The generality of the method was demonstrated by a range of selected lactones and amines.

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Key Words

amides, ring opening, Lewis acids, lactones, catalysis

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ID: J60-Y2008-0180