Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Org Biomol Chem. 2019 Oct 30;17(42):9305-9312. doi: 10.1039/c9ob02067e.
The chiral primary amine catalyzed asymmetric Michael reaction of thiazolones and α,β-unsaturated ketones was reported. Two different optimal catalytic systems were obtained corresponding to cyclic and linear α,β-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.
手性伯胺催化噻唑啉和α,β-不饱和酮的不对称迈克尔加成反应被报道。对于环状和线性α,β-不饱和酮，分别得到了两种不同的最优催化体系。通过使用手性伯胺作为催化剂和氨基酸衍生物作为添加剂，在手性和对映选择性（高达 95%的产率，所有都大于 19/1 dr，高达 96%ee）优异的情况下，以中等至良好的产率制备了多种含有噻唑环骨架的迈克尔加成产物。该反应进行了放大，以获得 1.73 克迈克尔加成产物，产率和立体选择性保持不变。
