文献类型：期刊文献

英文题名：Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

作者：Tong, Mengchao[1,2];Zhang, Yong[1,2];Qin, Cong[1,2];Fu, Yiwei[1,2];Liu, Yonghai[1,2];Li, Hao[1,2];Wang, Wei[1,2,3]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2018

卷号：5

期号：20

起止页码：2945

外文期刊名：ORGANIC CHEMISTRY FRONTIERS

收录：;EI(收录号：20184205941240);WOS:【SCI-EXPANDED(收录号:WOS:000448344700006)，CCR-EXPANDED(收录号:WOS:000448344700006)】；

基金：This work was supported by the National Natural Science Foundation of China (21572055, 21738002 and 21572054), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities and the China 111 Project (Grant B07023).

语种：英文

外文关键词：Microwave irradiation - Stereoselectivity

摘要：Alkenylazaarenes as a novel class of dipolarophiles for 1,3-dipolar cycloaddition (1,3-DC) with nitrones was reported. A regioselectivity-switchable synthesis of multisubstituted isoxazolidines had been developed. In the presence of TMSOTf as catalyst, 4-substituted isoxazolidines were obtained as major products with high regio- and diastereoselectivities. Nonetheless, under microwave irradiation in a sealed system with water as solvent, exclusive 5-substituted isoxazolidines were produced in good yields.