Modern medicinal chemistry widely exploits two structural motifs to improve physico-chemical characteristics of the compounds: fluorine atoms and small rings. Gem-difluorocyclopropanes combine both these structural features and are therefore considered as very promising building blocks for early drug discovery. A common approach to the construction of the gem-difluorocyclopropane core relies on the difluorocyclopropanation of alkenes. The Ruppert – Prakash reagent (CF3SiMe3) is one of the most convenient difluorocarbene equiavent to achieve that transformation; nevertheless, it was studied scarcely to date, mostly with non-functionalized substrates. In a series of works, we describe synthesis of various functionalized difluorocyclopropanes – valuable building blocks for medicinal chemistry. All scope and limitations, advantages and problems of the elaborated methodology would be discussed in the report.

New frontiers of difluorocyclopropanation of alkenes using Ruppert–Prakash reagent

2019 Spring National Meeting

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