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α,α′-C–H Bond Difunctionalization of Unprotected Alicyclic Amines

Daniel A. Valles, Subhradeep Dutta, Anirudra Paul, Khalil A. Abboud, Ion Ghiviriga, Daniel Seidel

2021Organic Letters25 citationsDOIOpen Access PDF

Abstract

A simple one-pot procedure enables the sequential, regioselective, and diastereoselective introduction of the same or two different substituents to the α- and α'-positions of unprotected azacycles. Aryl, alkyl, and alkenyl substituents are introduced via their corresponding organolithium compounds. The scope of this transformation includes pyrrolidines, piperidines, azepanes, and piperazines.

Topics & Concepts

Alicyclic compoundChemistryCyclic aminesBondCombinatorial chemistryMedicinal chemistryOrganic chemistryAmine gas treatingBusinessFinanceCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsRadical Photochemical Reactions
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