钴催化的对映选择性串联氢化反应精准合成手性 Z-烯丙酰胺。
Precise Synthesis of Chiral Z-Allylamides by Cobalt-Catalyzed Asymmetric Sequential Hydrogenations.
机构信息
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.
出版信息
Angew Chem Int Ed Engl. 2023 Apr 3;62(15):e202217871. doi: 10.1002/anie.202217871. Epub 2023 Feb 23.
Asymmetric sequential hydrogenations of conjugated enynes have been developed using a Ph-BPE-Co catalyst for the precise synthesis of chiral Z-allylamides in high activity (up to 1000 substrate/catalyst (S/C)) and with excellent enantioselectivity (up to >99 % enantiomeric excess (ee)). Mechanism experiments and theoretical calculations support a cationic Co /Co redox catalytic cycle. The catalytic activity difference between cobalt complexes of Ph-BPE and QuinoxP* was explained by the process decomposition of rate-determining step in the second hydrogenation.
已开发出使用 Ph-BPE-Co 催化剂的共轭烯炔的不对称顺序氢化反应，用于在高活性（高达 1000 倍底物/催化剂（S/C））下精确合成手性 Z-丙烯酰胺，并具有优异的对映选择性（高达> 99％对映体过量（ee））。机理实验和理论计算支持阳离子 Co / Co 氧化还原催化循环。Ph-BPE 和 QuinoxP* 的钴配合物之间的催化活性差异可以通过第二次氢化中速率决定步骤的过程分解来解释。
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