Journal ArticleDOI
Difluoro-Substituted Bicyclo[1.1.1]pentanes for Medicinal Chemistry: Design, Synthesis, and Characterization
Roman M. Bychek,Valeriia Hutskalova,Valeriia Hutskalova,Yuliya P Bas,Olga A. Zaporozhets,Sergey Zozulya,Vadym V. Levterov,Pavel K. Mykhailiuk,Pavel K. Mykhailiuk +8 more
TLDR
A practical synthetic approach to the difluoro-substituted bicyclo[1. 1.1.1]pentanes was developed, which are suggested as saturated bioisosteres of the benzene ring for drug discovery projects.Abstract:
A practical synthetic approach to the difluoro-substituted bicyclo[1.1.1]pentanes was developed. The key step was an addition of difluorocarbene (:CF2) to electron-rich bicyclo[1.1.0]butanes by the CF3TMS/NaI system. The obtained difluoro-bicyclo[1.1.1]pentanes are suggested to be used as saturated bioisosteres of benzene rings for the purpose of drug discovery projects.read more
Citations
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Journal ArticleDOI
Put a ring on it: application of small aliphatic rings in medicinal chemistry.
Matthias R. Bauer,Paolo Di Fruscia,Simon C. C. Lucas,Iacovos N Michaelides,Jennifer E. Nelson,R. Ian Storer,Benjamin C Whitehurst +6 more
TL;DR: A historical perspective and comparative up to date overview of commonly applied small rings, exemplifying key principles with recent literature examples and potential hazards and liabilities are illustrated and explained.
Journal ArticleDOI
Polarity-Reversal Strategy for the Functionalization of Electrophilic Strained Molecules via Light-Driven Cobalt Catalysis
TL;DR: This work presents a polarity-reversal strategy based on light-driven cobalt catalysis, which enables the generation of nucleophilic radicals through strain release and reveals deeper insight into mech-anism of the reaction.
Journal ArticleDOI
Photochemical C-F Activation Enables Defluorinative Alkylation of Trifluoroacetates and -Acetamides.
Mark W. Campbell,Viktor C. Polites,Shivani A. Patel,Juliette E. Lipson,Jadab Majhi,Gary A. Molander +5 more
TL;DR: In this paper, a photochemically mediated method for the defluorinative alkylation of a commodity feedstock: ethyl trifluoroacetate was identified using a previously developed diaryl ketone HAT catalyst.
Journal ArticleDOI
Water‐Soluble Non‐Classical Benzene Mimetics
Vadym V. Levterov,Yaroslav Panasyuk,Valentyna O. Pivnytska,Pavel K. Mykhailiuk,Pavel K. Mykhailiuk +4 more
TL;DR: Crystallographic analysis of 2-oxabicyclo[2.1.1]hexanes revealed that they occupy a novel chemical space, but at the same time resemble the fragment of meta -disubstituted benzenes.
Journal ArticleDOI
Strain release – an old tool for new transformations
TL;DR: This feature article focuses on strain-release driven strategies paying particular attention to the most recent (year > 2010) advances.
References
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