文献类型：期刊文献

英文题名：Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and α,β-unsaturated ketones

作者：Lu, Min[1];Li, Hong[1];Zou, Chuncheng[1];Li, Jianchang[1];Liu, Chengyu[1];Sun, Maolin[1];Ma, Yueyue[1];Cheng, Ruihua[1];Ye, Jinxing[1]

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

年份：2019

卷号：17

期号：42

起止页码：9305

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：;EI(收录号：20194507637757);WOS:【SCI-EXPANDED(收录号:WOS:000493539100005)，CCR-EXPANDED(收录号:WOS:000493539100005)】；

基金：This work was supported by the National Natural Science Foundation of China (21272068, 21572056, 21801077), the China Postdoctoral Science Foundation (2017M621382, 2018T110355), the Shanghai Sailing Program (18YF1406200), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：Addition reactions - Additives - Amines - Enantioselectivity - Ketones - Catalysis

摘要：The chiral primary amine catalyzed asymmetric Michael reaction of thiazolones and alpha,beta-unsaturated ketones was reported. Two different optimal catalytic systems were obtained corresponding to cyclic and linear alpha,beta-unsaturated ketones. By employing chiral primary amines as the catalysts and amino-acid derivatives as the additives, a variety of Michael adducts containing the scaffold of the thiazole ring were prepared in moderate to good yields and with excellent diastereo- and enantioselectivities (up to 95% yield, all up to >19/1 dr, up to 96% ee). The reaction was scaled up to obtain 1.73 grams of the Michael adduct with the maintenance of yield and stereoselectivity.