对映选择合成
动力学分辨率
对称化
羰基化
立体中心
化学
钴
催化作用
组合化学
废止
有机化学
一氧化碳
作者
Ming-Ya Teng,Yong‐Jie Wu,Jia-Hao Chen,Fan-Rui Huang,De-Yang Liu,Qi‐Jun Yao,Bing‐Feng Shi
标识
DOI:10.1002/anie.202318803
摘要
Transition metal-catalyzed enantioselective C-H carbonylation with carbon monoxide, an essential and easily available C1 feedstock, remains challenging. Here, we disclosed an unprecedented enantioselective C-H carbonylation catalyzed by inexpensive and readily available cobalt(II) salt. The reactions proceed efficiently through desymmetrization, kinetic resolution, and parallel kinetic resolution, affording a broad range of chiral isoindolinones in good yields with excellent enantioselectivities (up to 92 % yield and 99 % ee). The synthetic potential of this method was demonstrated by asymmetric synthesis of biological active compounds, such as (S)-PD172938 and (S)-Pazinaclone. The resulting chiral isoindolinones also serve as chiral ligands in cobalt-catalyzed enantioselective C-H annulation with alkynes to construct phosphorus stereocenter.
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