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A General and Modular Approach to BCP Alkylamines via Multicomponent Difunctionalization of [1.1.1]Propellane

Weichen Huang, Yongxiang Zheng, Sebastian Keeß, Gary A. Molander

2023Journal of the American Chemical Society74 citationsDOI

Abstract

-disubstituted benzenes. However, the limited approaches and requisite multistep syntheses of useful BCP building blocks are hampering early discovery research in medicinal chemistry. Herein we report the development of a modular strategy for the divergent preparation of functionalized BCP alkylamines. In this process, a general method to introduce fluoroalkyl groups to BCP scaffolds using readily available and easy-to-handle fluoroalkyl sulfinate salts was also developed. Moreover, this strategy can also be extended to S-centered radicals for incorporation of sulfones and thioethers into the BCP core. Overall, this multicomponent strategy enables rapid construction of BCP-type bioisosteres for applications in drug discovery.

Topics & Concepts

ChemistryPropellaneCombinatorial chemistryModular designPentaneBicyclic moleculeOrganic chemistryComputer scienceOperating systemSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsFluorine in Organic Chemistry