Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic)ketopiperazines using a readily affordable N-heterocyclic anhydride
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Functionalized 2-piperazinones play essential roles as conformationally-constrained peptidomimetics by mimicking inverse γ-turns in peptides. Here, we describe an efficient, scalable, stereoselective, modular, and chemoselective annulation protocol between a novel N-trifluoroacetyl anhydride and several reactive partners, including lactim ethers, imidoyl chlorides, aryl aldimines, and 1,3-azadienes, leading to vicinally functionalized (bicyclic) 2-piperazinones.
Moreno, A., & Beng, T. K. (2020). Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic)ketopiperazines using a readily affordable N-heterocyclic anhydride. Organic & Biomolecular Chemistry, 18(8), 1577–1581. https://doi.org/10.1039/d0ob00049c
Organic & Biomolecular Chemistry