Chai Guo-Li, Wang Xiao, Huang Wei-Yu, Hou Ya-Jing, Chang Junbiao
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
J Org Chem. 2024 Aug 16;89(16):11607-11619. doi: 10.1021/acs.joc.4c01319. Epub 2024 Aug 1.
A highly efficient asymmetric [3 + 2] cycloaddition reaction of 2'-hydroxychalcones with -2,2,2-trifluoroethylisatin ketimines catalyzed by a ()-3,3'-I-BINOL-boron complex was developed. A broad range of 3,2'-pyrrolidinyl spirooxindole derivatives bearing a CF-substituted pyrrolidine moiety with four contiguous stereocenters was prepared in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). This protocol had the characteristics of mild reaction conditions, high efficiency, and excellent stereocontrol.
开发了一种由()-3,3'-I-BINOL-硼配合物催化的2'-羟基查尔酮与-2,2,2-三氟乙基异吲哚酮亚胺的高效不对称[3+2]环加成反应。制备了一系列带有CF-取代吡咯烷部分且具有四个相邻立体中心的3,2'-吡咯烷基螺环氧化吲哚衍生物，产率高，非对映选择性和对映选择性优异（高达>20:1的非对映体比例和>99%的对映体过量）。该方法具有反应条件温和、效率高和立体控制优异的特点。
