文献类型：期刊文献

英文题名：γ′-Selective Functionalization of Cyclic Enones: Construction of a Chiral Quaternary Carbon Center by [4+2] Cycloaddition/Retro-Mannich Reaction with 3-Substituted Maleimides

作者：Zou, Chuncheng[1];Zeng, Chuikun[1];Liu, Zhen[2];Lu, Min[1];Sun, Xiaohua[1];Ye, Jinxing[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Engn Res Ctr Pharmaceut Proc Chem, Minist Educ,Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Chem Engn, Shanghai 200237, Peoples R China

年份：2016

卷号：55

期号：46

起止页码：14255

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20164502992918);WOS:【SCI-EXPANDED(收录号:WOS:000387028000007)，CCR-EXPANDED(收录号:WOS:000387028000007)】；

基金：This work was supported by the National Natural Science Foundation of China (21272068, 21572056), the Program for New Century Excellent Talents in University (NCET-13-0800), the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：asymmetric catalysis; cycloaddition; DFT calculations; isomerization; organocatalysis

摘要：The first example of organocatalyzed gamma'-selective functionalization of cyclic enones with 3-substituted male-imides results in the stereoselective construction quaternary carbon center is presented. The reactions provided gamma'-functionalized cyclic enones and beta-functionalized cyclopentenones in good to excellent yields with excellent diastereo- and enantio-selectivities. DFT calculations indicated that the reaction might proceed as a [4+2] cycloaddition/retro-Mannich reaction which could explain the unexpected product with a chiral quaternary carbon center and the excellent stereoselectivity.