硼酸化
铱
化学
对映选择合成
催化作用
取代基
组合化学
配体(生物化学)
小分子
吡啶
酰胺
分子
反应性(心理学)
氢键
有机化学
立体化学
药物化学
医学
替代医学
病理
芳基
受体
烷基
生物化学
作者
Ronald L. Reyes,Miyu Sato,Tomohiro Iwai,Kimichi Suzuki,Satoshi Maeda,Masaya Sawamura
出处
期刊:Science
[American Association for the Advancement of Science]
日期:2020-08-21
卷期号:369 (6506): 970-974
被引量:101
标识
DOI:10.1126/science.abc8320
摘要
Site selectivity and stereocontrol remain major challenges in C-H bond functionalization chemistry, especially in linear aliphatic saturated hydrocarbon scaffolds. We report the highly enantioselective and site-selective catalytic borylation of remote C(sp3)-H bonds γ to the carbonyl group in aliphatic secondary and tertiary amides and esters. A chiral C-H activation catalyst was modularly assembled from an iridium center, a chiral monophosphite ligand, an achiral urea-pyridine receptor ligand, and pinacolatoboryl groups. Quantum chemical calculations support an enzyme-like structural cavity formed by the catalyst components, which bind the substrate through multiple noncovalent interactions. Versatile synthetic utility of the enantioenriched γ-borylcarboxylic acid derivatives was demonstrated.
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