用于合成双螺[苯并噻吩酮-茚二酮-吡咯烷]衍生物的有机催化对映选择性[3+2]环加成反应
Organocatalyzed Enantioselective [3+2] Cycloaddition Reactions for Synthesis of Dispiro[benzothiophenone-indandione-pyrrolidine] Derivatives.
作者信息
Liu Hong-Yan, Du Da-Ming
机构信息
School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No. 5 Zhongguancun South Street, Beijing 100081, China.
Key Laboratory of Medicinal Molecule Science and Pharmaceutical Technology, Ministry of Industry and Information Technology, No. 5 Zhongguancun South Street, Beijing 100081, China.
出版信息
Molecules. 2024 Oct 13;29(20):4856. doi: 10.3390/molecules29204856.
An organocatalytic enantioselective [3+2] cycloaddition reaction involving 2-arylidene-1,3-indandiones and -2,2-difluoroethylbenzothiophenone imines was developed. This approach efficiently afforded dispiro[benzothiophenone-indandione-pyrrolidine]s, featuring three stereocenters, in 84-98% yields with 3-93% ee and 9:1->20:1 dr. Notably, the method maintained its yield and enantioselectivity integrity even in a gram-scale amplification experiment. For example, the product with substituents on aromatics were obtained in 90% yield with 91% ee and >20:1 dr. Its absolute configuration was established through X-ray single-crystal diffraction analysis, and a plausible reaction mechanism was proposed.
开发了一种涉及2-亚芳基-1,3-茚二酮和-2,2-二氟乙基苯并噻吩酮亚胺的有机催化对映选择性[3+2]环加成反应。该方法以84-98%的产率、3-93%的对映体过量（ee）和9:1->20:1的非对映体比例（dr），高效地得到了具有三个立体中心的双螺[苯并噻吩酮-茚二酮-吡咯烷]。值得注意的是，即使在克级放大实验中，该方法仍能保持其产率和对映选择性的完整性。例如，芳环上带有取代基的产物以90%的产率、91%的ee和>20:1的dr得到。通过X射线单晶衍射分析确定了其绝对构型，并提出了合理的反应机理。
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