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

Roman M Bychek; Valeriia Hutskalova; Yuliya P Bas; Olga A Zaporozhets; Sergey Zozulya; Vadym V Levterov; Pavel K Mykhailiuk

doi:10.1021/acs.joc.9b01947

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

J Org Chem. 2019 Dec 6;84(23):15106-15117. doi: 10.1021/acs.joc.9b01947. Epub 2019 Oct 7.

Authors

Roman M Bychek¹, Valeriia Hutskalova^{1

2}, Yuliya P Bas², Olga A Zaporozhets², Sergey Zozulya^{1

3}, Vadym V Levterov¹, Pavel K Mykhailiuk^{1

2}

Affiliations

¹ Enamine Ltd. , Chervonotkatska 78 , Kyiv 02094 , Ukraine.
² Taras Shevchenko National University of Kyiv , Chemistry Department , Volodymyrska 64 , Kyiv 01601 , Ukraine.
³ Bienta , Chervonotkatska 78 , Kyiv 02094 , Ukraine.

PMID: 31553875
DOI: 10.1021/acs.joc.9b01947

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.

Publication types

Research Support, Non-U.S. Gov't