文献类型：期刊文献

英文题名：Highly Enantioselective Michael Addition of Aromatic Ketones to Nitrodienes and the Application to the Synthesis of Chiral γ-Aminobutyric Acid

作者：Guo, Xing-Tao;Sha, Feng;Wu, Xin-Yan[1]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2017

卷号：49

期号：3

起止页码：647

外文期刊名：SYNTHESIS-STUTTGART

收录：;EI(收录号：20164002861098);WOS:【SCI-EXPANDED(收录号:WOS:000393233000023)，CCR-EXPANDED(收录号:WOS:000393233000023)】；

基金：We are grateful for the financial support from National Natural Science Foundation of China (Nos. 21242007, 21102043), Science and Technology Commission of Shanghai Municipality (Nos. 15ZR1409200), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：chiral primary amine-thiourea; enantioselective catalysis; ketone; Michael addition; nitrodiene

摘要：A highly enantioselective Michael addition of aromatic ketones to alpha,beta,gamma,delta-unsaturated nitro compounds is described. In the presence of a chiral primary amine-thiourea based on dehydroabietic amine, gamma-nitro ketones were obtained in excellent enantioselectivities (up to 95% ee) with up to 95% yield. In addition, this methodology has been successfully applied in the asymmetric synthesis of chiral 3-(aminomethyl)-5-phenylpentanoic acid.