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Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic)ketopiperazines using a readily affordable N-heterocyclic anhydride

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Abstract

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.

Graphical abstract: Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic)ketopiperazines using a readily affordable N-heterocyclic anhydride

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Article information


Submitted
09 Jan 2020
Accepted
05 Feb 2020
First published
05 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic)ketopiperazines using a readily affordable N-heterocyclic anhydride

A. Moreno and T. K. Beng, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00049C

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