Last of the gem‐Difluorocycloalkanes 2: Synthesis of Fluorinated Cycloheptane Building Blocks

The gem‐difluorocycloalkane family was extended to all possible regioisomers of the gem‐difluorocycloheptane, monofunctionalized by carboxilic‐, amino‐ or keto‐ group, that were synthesized on a multigram scale. The preparation of the corresponding building blocks was achieved from readily accessibl...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-12, Vol.2021 (47), p.6561-6569
Main Authors: Herasymchuk, Maksym, Melnykov, Kostiantyn P., Yarmoliuk, Dmytro V., Serhiichuk, Dmytro, Rotar, Valeriia, Pukhovoi, Timur, Kuchkovska, Yuliya O., Holovach, Sergey, Volochnyuk, Dmitriy M., Ryabukhin, Sergey V., Grygorenko, Oleksandr O.
Format: Article
Language:English
Subjects:
Building blocks
Cycloalkane
Cycloheptane
Deoxofluorination
Fluorine
Homology
Ketones
Rings (mathematics)
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Summary:The gem‐difluorocycloalkane family was extended to all possible regioisomers of the gem‐difluorocycloheptane, monofunctionalized by carboxilic‐, amino‐ or keto‐ group, that were synthesized on a multigram scale. The preparation of the corresponding building blocks was achieved from readily accessible starting materials either via six‐membered ring homologation or deoxofluorination of the appropriate seven‐membered cyclic ketones. A series of isomeric gem‐difluorocycloheptane derivatives were obtained in two to six synthetic steps from readily available starting materials. The developed synthetic approaches were shown to be efficient for a multigram‐scale synthesis of target compounds and involved six‐membered ring homologation and/or deoxofluorination reactions as the key steps.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001530