文献类型：期刊文献

英文题名：Asymmetric Construction of 3,4-Diamino Pyrrolidines via Chiral N,O-Ligand/Cu(I) Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Phthalimidonitroethene

作者：He, Fu-Sheng;Zhu, Han;Wang, Zheng;Gao, Ming;Yu, Xingxin[1];Deng, Wei-Ping[1]

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

年份：2015

卷号：17

期号：20

起止页码：4988

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000363225000015)，CCR-EXPANDED(收录号:WOS:000363225000015)】；

基金：This work is supported by The Fundamental Research Funds for the Central Universities, the National Natural Science Foundation of China (No. 21172068), Shanghai Pujiang Program (No. 14PJD013), and Shanghai Yangfan Program (No. 14YF1404600).

语种：英文

摘要：A series of chiral N,O-ligands derived from a 1,2-dihydroimidazo[1,2-a]quinolone motif have been evaluated for the asymmetric 1,3-dipolar cydoaddition of azomethine ylides with a novel dipolarophile beta-phthalimidonitroethene. A newly designed DHIPOH ligand 7c bearing 1-methyl and 4-iodo substituents was found to have significant "synergistic steric effects" and consequently afforded the corresponding 4-nitro-3-aminopyrrolidines with excellent diastereo- (dr up to 98:2) and enantio selectivities (ee up to 99%). Subsequent Raney Ni-catalyzed reduction and deprotection of phthalyl led to the structurally and biologically important 3,4-diaminopyrrolidines in a straightforward and efficient pathway.