文献类型：期刊文献

英文题名：Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides

作者：Zhao, Mei-Xin[1,2];Xiang, Juan[1,2];Zhao, Zi-Qiang[1,2];Zhao, Xiao-Li[3];Shi, Min[1,2,4]

机构：[1]East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[3]East China Normal Univ, Dept Chem, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

年份：2020

卷号：18

期号：8

起止页码：1637

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20201008257187);WOS:【SCI-EXPANDED(收录号:WOS:000519705100015)，CCR-EXPANDED(收录号:WOS:000519705100015)】；

基金：We are grateful for financial support from the National Natural Science Foundation of China (21272067), the Natural Science Foundation of Shanghai (15ZR1411900) and the Fundamental Research Funds for the Central Universities (222201717003).

语种：英文

外文关键词：Quinone

摘要：A catalytic asymmetric synthesis of 3,4-dihydrocoumarins with adjacent tertiary-quaternary stereocenters by 1,6-addition/transesterification cascade reaction of alpha-isocyanoacetates with ortho-hydroxyphenyl-substituted para-quinone methides (p-QMs) has been developed. Using a combination of dihydroquinidine-derived aminophosphine and silver nitrate as a binary catalytic system, moderate to good yields, excellent diastereoselectivities (>20 : 1 dr) and good to excellent enantioselectivities (up to 94% ee) were achieved for a wide range of isocyanoacetates and p-QMs.