环状磺酰基酮亚胺与异吲哚酮衍生酮亚胺之间的对映选择性曼尼希反应
Enantioselective Mannich Reaction between Cyclic -Sulfonyl Ketimines and Isatin-Derived Ketimines.
作者信息
Mei Yao-Yao, Xu Chong-Xiao, Sha Feng, Hao Shilong, Liu Shunying, Wu Xin-Yan
机构信息
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China.
出版信息
J Org Chem. 2024 Sep 20;89(18):13272-13283. doi: 10.1021/acs.joc.4c01405. Epub 2024 Sep 9.
An enantioselective Mannich reaction with cyclic -sulfonyl ketimines as the nucleophiles was developed. In the presence of 5 mol % chiral thiourea catalyst , the asymmetric Mannich reaction between cyclic -sulfonyl ketimines and isatin-derived ketimines was achieved in high yields and good-to-excellent enantioselectivities (84-99% yields with 75-99.8% ee). This methodology provided an effective route to construct chiral 3-amino-2-oxindoles containing a cyclic -sulfonyl ketimine scaffold. The initial biological evaluation of the products in cell-based assays demonstrated that some compounds have excellent antiproliferative activity against human osteosarcoma cells.
开发了一种以环状磺酰基酮亚胺为亲核试剂的对映选择性曼尼希反应。在5 mol%手性硫脲催化剂存在下，环状磺酰基酮亚胺与异吲哚酮衍生的酮亚胺之间的不对称曼尼希反应以高产率和良好至优异的对映选择性实现（产率84 - 99%，对映体过量值75 - 99.8%）。该方法为构建含有环状磺酰基酮亚胺支架的手性3-氨基-2-氧化吲哚提供了一条有效途径。基于细胞试验对产物进行的初步生物学评价表明，一些化合物对人骨肉瘤细胞具有优异的抗增殖活性。
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