Institute of Pharmacology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China.
J Org Chem. 2021 Sep 17;86(18):13011-13024. doi: 10.1021/acs.joc.1c01705. Epub 2021 Sep 8.
An amino-controlled regiodivergent asymmetric synthesis of CF-containing spiro-pyrrolidine-pyrazolone compounds is described. With alkaloid-derived squaramide as catalyst, the 1,3-dipolar cycloaddition of α,β-unsaturated pyrazolone with diethyl 2-((2,2,2-trifluoroethyl)imino) malonate offered adducts in excellent yields, dr, and ee. While the cyclohexanediamine-derived squaramide was employed, the reaction afforded a series of structure isomers through a switched umpolung reaction.
本文描述了一种含氟螺吡咯烷-吡唑啉酮化合物的手性氨基调控区域发散不对称合成方法。以生物碱衍生的手性双酰胺作为催化剂，α,β-不饱和吡唑啉酮与二乙基 2-((2,2,2-三氟乙基)亚氨基)丙二酸酯的 1,3-偶极环加成反应以优异的产率、dr 和 ee 得到加成产物。而当使用环己二胺衍生的手性双酰胺时，反应通过反转极性反应得到一系列结构异构体。
