Hu Yang, Yuan Jie, Li Zheyao, Zhao Lin, Zhao Jianhong, Yu Xinhong
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & Technology, Shanghai, People's Republic of China.
State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology, Shanghai, 200237, People's Republic of China.
Commun Chem. 2022 Sep 6;5(1):106. doi: 10.1038/s42004-022-00695-3.
Chiral benzo five-membered heterocyclic spirocyclopropanes are an important class of parent core structures with pharmacological activity. A novel organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spirocyclopropylation of benzofuran-2-ones and indolin-2-ones from allyl tert-butyl ethers/ pent-2,4-dienyl ethyl ethers with excellent enantioselectivity (ee% up to > 99) and diastereoselectivity(dr.% up to 91:9) has been developed. This process involves the successful dynamic kinetic resolution of racemic 3-bromobenzofuran-2-ones or 3-bromoindolin-2-ones. Its synthetic application will provide a new aminocatalytic cascade tool for the efficient synthesis of complex molecules.
手性苯并五元杂环螺环丙烷是一类具有药理活性的重要母体核心结构。已开发出一种新型有机催化一锅串联醚氧化亚胺离子活化策略，用于从烯丙基叔丁基醚/戊-2,4-二烯基乙醚对苯并呋喃-2-酮和吲哚啉-2-酮进行不对称螺环丙烷化反应，具有优异的对映选择性（对映体过量百分比高达>99）和非对映选择性（非对映体比例高达91:9）。该过程涉及外消旋3-溴苯并呋喃-2-酮或3-溴吲哚啉-2-酮的成功动态动力学拆分。其合成应用将为复杂分子的高效合成提供一种新的氨基催化串联工具。
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