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2. A convenient synthesis of CHF2O-containing pyrrolidines and related compounds — Perspective building blocks for drug discovery

Author

Kostiantyn Levchenko, Ivan Virstiuk, Daria Menshykova, and Nazariy Pokhodylo

Subjects
Chemistry, QD1-999
Abstract

Fluorine-containing organic molecules, including CHF2O-derivatives, are among the most sought-after in medicinal chemistry. In the current work, a mini-library of 21 compounds with a CHF2O-motif incorporated with azetidine, pyrrolidine (proline), piperidine, 2-azabicyclo[2.2.1]heptane, and 8-azabicyclo[3.2.1]octane cores were synthesized. A multigram scale (10 to 30 g) procedure for synthesizing title compounds from commercially available amino alcohols was studied.

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3. ChemInform Abstract: Copper-Catalyzed O-Difluoromethylation of Functionalized Aliphatic Alcohols: Access to Complex Organic Molecules with an OCF2H Group

Author

Pavel K. Mykhailiuk, Olexandr P. Datsenko, Oleh Serhiichuk, Kostiantyn Levchenko, Viktor O. Iaroshenko, and Andrei A. Tolmachev

Subjects
chemistry.chemical_compound, chemistry, Drug discovery, Group (periodic table), Functional group, Copper catalyzed, General Medicine, Combinatorial chemistry, High potential, Organic molecules
Abstract

A two-step synthetic strategy toward difluoromethyl ethers via a CuI-catalyzed reaction of the alcohols, bearing additional protected functionalities, with FSO2CF2CO2H has been developed. The high potential of the developed protocol has been shown by preparing novel OCF2H-analogues of GABA and l-proline. The described transformation has good functional group compatibility and can serve as a powerful synthetic tool for late-stage preparation of complex OCF2H-containing organic compounds as well as building blocks for drug discovery.

Published
2016
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4. Copper-Catalyzed O-Difluoromethylation of Functionalized Aliphatic Alcohols: Access to Complex Organic Molecules with an OCF2H Group

Author

Oleh Serhiichuk, Viktor O. Iaroshenko, Pavel K. Mykhailiuk, Andrei A. Tolmachev, Kostiantyn Levchenko, and Olexandr P. Datsenko

Subjects
010405 organic chemistry, Drug discovery, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Chemical reaction, Combinatorial chemistry, 0104 chemical sciences, Organic molecules, chemistry.chemical_compound, chemistry, Group (periodic table), Functional group, Copper catalyzed, Organic chemistry, High potential
Abstract

A two-step synthetic strategy toward difluoromethyl ethers via a CuI-catalyzed reaction of the alcohols, bearing additional protected functionalities, with FSO2CF2CO2H has been developed. The high potential of the developed protocol has been shown by preparing novel OCF2H-analogues of GABA and l-proline. The described transformation has good functional group compatibility and can serve as a powerful synthetic tool for late-stage preparation of complex OCF2H-containing organic compounds as well as building blocks for drug discovery.

Published
2016

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