文献类型：期刊文献

英文题名：Stereoselective Synthesis of Pyrrolidines Containing a 3-Fluoro Quaternary Stereocenter via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition

作者：Liu, Yang-Zi;Shang, Shao-Jing;Yang, Wu-Lin;Luo, Xiaoyan[1];Deng, Wei-Ping[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2017

卷号：82

期号：20

起止页码：11141

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20174304305529);WOS:【SCI-EXPANDED(收录号:WOS:000413710100037)，CCR-EXPANDED(收录号:WOS:000413710100037)】；

基金：This work was supported by the National Natural Science Foundation of China (Nos. 21372074, 21572053).

语种：英文

外文关键词：Catalysis - Stereochemistry - Stereoselectivity - Synthesis (chemical)

摘要：A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to beta,beta-disubstituted beta-fluoroacrylates catalyzed by a chiral N,O-ligand/Cu(CH3CN)(4)BF4 system is reported, affording chiral densely substituted pyrrolidines with four contiguous stereocenters, including one fluorinated quaternary stereocenter at the 3-position, in good to excellent yields (up to 99%), with excellent levels of diastereo- and enantioselectivities (dr >20:1; ee up to 99%).