School of Pharmacy and Shanghai Key Laboratory of New Drug Design , East China University of Science and Technology , 130 Meilong Road , Shanghai 200237 , China.
Org Lett. 2018 Jul 6;20(13):3838-3842. doi: 10.1021/acs.orglett.8b01430. Epub 2018 Jun 14.
A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with 3-silyl unsaturated esters has been developed, providing elegant access to chiral 3-silylpyrrolidine derivatives bearing contiguous stereogenic centers in moderate-to-excellent yields (up to 99%) with high diastereo- and enantioselectivities (dr up to >99:1; ee up to 96%). Notably, the 3-silylpyrrolidines can easily be converted to pyrrolidine azasugar derivatives with potential biological activities by the reduction of two ester groups and carbon-silicon bond oxidation.
发展了一种高效的铜（I）催化不对称 1,3-偶极环加成反应，使亚胺叶立德与 3-硅基不饱和酯反应，以中等至优秀的收率（高达 99%）和高的非对映选择性和对映选择性（dr 高达>99:1；ee 高达 96%）提供了手性 3-硅基吡咯烷衍生物。值得注意的是，通过还原两个酯基和碳-硅键氧化，3-硅基吡咯烷很容易转化为具有潜在生物活性的吡咯烷氮杂糖衍生物。
