Wang Zhen-Hua, Liu Ji-Hong, Zhang Yan-Ping, Zhao Jian-Qiang, You Yong, Zhou Ming-Qiang, Han Wen-Yong, Yuan Wei-Cheng
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.
School of Pharmacy, Zunyi Medical University, Zunyi 563006, China.
Org Lett. 2022 Jun 10;24(22):4052-4057. doi: 10.1021/acs.orglett.2c01510. Epub 2022 May 27.
With a Cu(OTf)/chiral ferrocenyl P,N-ligand complex as a catalyst, the enantioselective desymmetrization of -arylmaleimides was successfully realized by taking advantage of the asymmetric 1,3-dipolar cycloaddition reaction of -2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse FC-containing octahydropyrrolo[3,4-]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C-N axial bond, were obtained with excellent results (≤99% yield, >20:1 dr, and 99% ee).
以Cu(OTf)/手性二茂铁基P,N-配体络合物为催化剂，通过利用α-2,2,2-三氟乙基异吲哚酮亚胺的不对称1,3-偶极环加成反应，成功实现了α-芳基马来酰亚胺的对映选择性去对称化反应。得到了一系列结构多样的含氟八氢吡咯并[3,4-b]吡咯，其具有四个相邻的碳立体中心和一个立体异构的手性C-N轴键，反应结果优异（产率≤99%，非对映体比例>20:1，对映体过量值99%）。
