文献类型：期刊文献

英文题名：Asymmetric Construction of 3-Azabicyclo[3.1.0]hexane Skeleton with Five Contiguous Stereogenic Centers by Cu-Catalyzed 1,3-Dipolar Cycloaddition of Trisubstituted Cyclopropenes

作者：Deng, Hua[1,2];Yang, Wu-Lin[1,2];Tian, Fei[1,2];Tang, Wenjun[1,2,3];Deng, Wei-Ping[1,2,3]

机构：[1]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Ctr Excellence Mol Synth, 345 Ling Ling Rd, Shanghai 200032, Peoples R China

年份：2018

卷号：20

期号：13

起止页码：4121

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000438469500092)，CCR-EXPANDED(收录号:WOS:000438469500092)】；

基金：This work was supported by the National Natural Science Foundation of China (No. 21772038), Shanghai Sailing Program (No. 18YF140560), and the Fundamental Research Funds for the Central Universities.

语种：英文

摘要：A highly diastereo- and enantioselective desymmetrization of prochiral cyclopropenes via a Cu(CH3CN)(4)BF4/Ph-Phosferrox complex catalyzed 1,3-dipolar cycloaddition of azomethine ylides was described. A variety of complex 3-azabicyclo[3.1.0]hexane derivatives bearing five contiguous stereogenic centers and two all-carbon quaternary stereogenic centers were directly synthesized as a single isomer in excellent yields (up to 99%) and enantioselectivities (97 -> 99% ee). Notably, various functional groups (CO2R, CN, CONMe2, and Ph) of cyclopropenes were found to be well-tolerated in this transformation. The cycloadduct was conveniently converted to a biologically important GABA derivative via LiAlH4 reduction and subsequent hydrolysis.