期刊
CHINESE CHEMICAL LETTERS
卷 34, 期 5, 页码 -出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2022.107894
关键词
Palladiumcatalyst; Axially chiral; Acetylation; Dibenzophosphorus oxide
Here, we present the first atroposelective acyloxylation of a C(sp2)-H bond using a phosphine oxide directing group. Surprisingly, this reaction proceeds via an eight-membered palladacycle intermediate instead of the more favored five-membered palladacycle. Additionally, we found that L-pGlu-OH, a readily available chiral amino acid derivative, is the best chiral ligand for promoting this atroposelective remote C-H functionalization reaction.
Herein, we report the first atroposelective C(sp2)-H bond acyloxylation enabled by a phosphine oxide di-recting group. Uniquely, this transformation is shown to proceed through an eight-membered palladacycle intermediate, as opposed to the kinetically and thermodynamically favored five-membered palladacycle intermediate. Additionally, L-pGlu-OH, a cheap and abundant chiral amino acid derivative, was identified as the best chiral ligand to promote this atroposelective remote C -H functionalization reaction. (c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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