College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P.R. China.
Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P.R. China.
Org Lett. 2020 Oct 2;22(19):7427-7432. doi: 10.1021/acs.orglett.0c02394. Epub 2020 Sep 23.
Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of β-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized β-alkynyl-β-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable β-alkynyl-β-amino carbonyl scaffolds.
readily available potassium alkynyltrifluoroborates 被用于 organocatalytic asymmetric conjugate alkynylation 的 β-enaminones。modified binaphthol 催化剂和 in situ 生成的 organodifluoroboranes 的截获被证明对获得功能化的 β-alkynyl-β-amino carbonyls 和衍生物很重要，这些衍生物具有改进的 chemo-reactivity 和 enantio-induction。mechanistic 研究揭示了分子筛对效率和立体控制的影响。产物进一步进行官能团化，生成了一系列有价值的 β-alkynyl-β-amino carbonyl 支架。
