期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 -, 期 -, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202303948
关键词
C-H Functionalization; Cyclobutanes; Diastereocontrol; Ligand; Palladium
The study presents a sequential C-H/C-C functionalization strategy for the stereospecific synthesis of cis-gamma-functionalized cyclobutyl ketones from readily available cyclobutyl aryl ketones. This strategy involves the generation of a bicyclo[1.1.1]pentan-2-ol intermediate from the parent cyclobutyl ketone via an optimized Norrish-Yang procedure, followed by a ligand-enabled, palladium-catalyzed C-C cleavage/functionalization to produce valuable cis-gamma-(hetero)arylated, alkenylated, and alkynylated cyclobutyl aryl ketones. The benzoyl moiety of these compounds can be further converted to a wide range of functional groups, including amides and esters.
1,3-Difunctionalized cyclobutanes are an emerging scaffold in medicinal chemistry that can confer beneficial pharmacological properties to small-molecule drug candidates. However, the diastereocontrolled synthesis of these compounds typically requires complicated synthetic routes, indicating a need for novel methods. Here, we report a sequential C-H/C-C functionalization strategy for the stereospecific synthesis of cis-gamma-functionalized cyclobutyl ketones from readily available cyclobutyl aryl ketones. Specifically, a bicyclo[1.1.1]pentan-2-ol intermediate is generated from the parent cyclobutyl ketone via an optimized Norrish-Yang procedure. This intermediate then undergoes a ligand-enabled, palladium-catalyzed C-C cleavage/functionalization to produce valuable cis-gamma-(hetero)arylated, alkenylated, and alkynylated cyclobutyl aryl ketones, the benzoyl moiety of which can subsequently be converted to a wide range of functional groups including amides and esters.
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