Normandie University, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.
Key Laboratory of Organosilicon Chemistry and, Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou, P. R. China.
Chemistry. 2018 Apr 11;24(21):5644-5651. doi: 10.1002/chem.201706167. Epub 2018 Mar 15.
The first catalytic asymmetric synthesis of highly functionalized pentafluorosulfanylated pyrrolidines is described. The method, based on a 1,3-dipolar cycloaddition reaction of aryl and heteroaryl-substituted glycine Schiff bases with pentafluorosulfanyl acrylic esters, gave access to a broad range of pyrrolidines bearing aryl, naphtyl, and heteroaryl groups. By using Xing-Phos as a catalyst, the corresponding products were obtained in good yields, good to high regioselectivity, and excellent diastereo- and enantioselectivities (up to 98 % ee). This methodology allowed the preparation of enantioenriched SF compounds for the first time using an enantioselective approach.
首次描述了高官能化五氟硫基化吡咯烷的催化不对称合成。该方法基于芳基和杂芳基取代甘氨酸席夫碱与五氟硫基丙烯酸酯的 1,3-偶极环加成反应，可获得广泛的带有芳基、萘基和杂芳基的吡咯烷。使用 Xing-Phos 作为催化剂，相应的产物以良好的收率、良好至高的区域选择性以及优异的非对映选择性和对映选择性（高达 98%ee）获得。该方法首次使用对映选择性方法制备了手性富集的 SF 化合物。
