文献类型：期刊文献

英文题名：Elaboration of phosphoramidite ligands enabling palladiumcatalyzed diastereo- and enantioselective all carbon [4+3] cycloaddition

作者：Zheng, Xing[1];Sun, Hao[1];Yang, Wu-Lin[1];Deng, Wei-Ping[1]

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

年份：2020

卷号：63

期号：7

起止页码：911

外文期刊名：SCIENCE CHINA-CHEMISTRY

收录：;EI(收录号：20201608413593);WOS:【SCI-EXPANDED(收录号:WOS:000524395100001)，CCR-EXPANDED(收录号:WOS:000524395100001)】；

基金：This work is supported by the National Natural Science Foundation of China (21772038, 21971062). We greatly appreciate the Research Center of Analysis and Test of East China University of Science and Technology for the assistance with the MS and NMR analysis.

语种：英文

外文关键词：asymmetric catalysis; [4+3] cycloaddition; electron-deficient dienes; palladium

摘要：A palladium-catalyzed diastereo- and enantioselective all carbon [4+3] cycloaddition of trimethylenemethane was developed by employing the elaborate tetrahydroquinoline-derived phosphoramidite ligand. The exclusive regioselectivity was realized by using the aromatization-driven diene indole-2,3-quinodimethanes, affording biologically important cyclohepta[b]indoles with excellent diastereo-, and enantioselectivities (up to >20:1 dr, >99% ee). Furthermore, the more challenging pyrrolidone-3,4-dienes, in the absence of aromatization force, were also compatible inthereaction, providing novel cyclohepta[c]pyrrol-1(2H)-ones with excellent regio-, diastereo-, and enantioselectivities (up to >20:1 rr, >20:1 dr, >99% ee).