文献类型：期刊文献

英文题名：Enantioselective direct Mannich reactions of 3-substituted oxindoles catalyzed by chiral phosphine via dual-reagent catalysis

作者：Jin, Qiaowen[1];Zheng, Changwu[2];Zhao, Gang[2];Zou, Gang[1]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

年份：2018

卷号：74

期号：30

起止页码：4134

外文期刊名：TETRAHEDRON

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000439402100014)，CCR-EXPANDED(收录号:WOS:000439402100014)】；

基金：Financial support from Chinese Academy of Sciences (XDB 20020100) and the National Natural Science Foundation of China (Nos. 21272247, 21572247, 21290184) is gratefully acknowledged.

语种：英文

外文关键词：Mannich-type reactions; Nucleophilic phosphines; Dual-reagent catalysis

摘要：A combination of an amino acid-derived chiral phosphine catalyst and methyl acrylate to catalyze the direct Mannich reaction of 3-substituted oxindoles and imines has been reported to afford 3-tetrasubstituted oxindole derivatives which are key structures for biological activities. The products are formed with a quaternary carbon and featured with two adjacent chiral centers. Various N-EDG(electron-donating group) and N-EWG(electron-withdrawing group) protected oxindoles, including 3-aryl and 3-alkyl substituted ones, have been evaluated with aromatic and aliphatic imines under this catalytic system, smoothly giving desired products in good yields as well as excellent diastereo- and enantioselectivities. (C) 2018 Elsevier Ltd. All rights reserved.