Difluoro-Substituted Bicyclo[1.1.1]pentanes for Medicinal Chemistry: Design, Synthesis, and Characterization

2019171 citationsJournal Article

Authors

Roman Bychek · Enamine (Ukraine)

Valeriia Hutskalova · Taras Shevchenko National University of Kyiv

Yuliya P. Bas · Taras Shevchenko National University of Kyiv

Olga A. Zaporozhets · Taras Shevchenko National University of Kyiv

Sergey Zozulya · Enamine (Ukraine)

Vadym V. Levterov · Enamine (Ukraine)

Pavel K. Mykhailiuk

Abstract

A practical synthetic approach to the difluoro-substituted bicyclo[1.1.1]pentanes was developed. The key step was an addition of difluorocarbene (:CF<sub>2</sub>) to electron-rich bicyclo[1.1.0]butanes by the CF<sub>3</sub>TMS/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.

Topics & Keywords

Fluorine in Organic Chemistry Cyclopropane Reaction Mechanisms Synthesis and Reactions of Organic Compounds

Publication Details

Published in: The Journal of Organic Chemistry

Volume 84, Issue 23, pp. 15106-15117

DOI: 10.1021/acs.joc.9b01947

Field-Weighted Citation Impact: 5.01

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Difluoro-Substituted Bicyclo[1.1.1]pentanes for Medicinal Chemistry: Design, Synthesis, and Characterization

Authors

Abstract

Topics & Keywords

Publication Details