School of Chemistry and Chemical Engineering, Beijing Institute of Technology , Beijing 100081, People's Republic of China.
Org Lett. 2017 Mar 3;19(5):1036-1039. doi: 10.1021/acs.orglett.6b03846. Epub 2017 Feb 15.
A novel bifunctional squaramide-catalyzed one-pot electrophilic trifluoromethylthiolation-sulfur-Michael/aldol cascade reaction for the construction of CFS-containing spiro-cyclopentanone-thiochromanes was developed. This convenient, one-pot cascade reaction serves as a powerful tool for the enantioselective construction of potential bioactive spiro-cyclopentanone-thiochromanes, which have one quaternary stereocenter containing a CFS group and three contiguous stereocenters including one spiro all-carbon quaternary center, in moderate to good yields with excellent stereoselectivities (up to 15:1 dr, >99% ee). The synthetic transformations of the resulting products were also be achieved.
一种新型的双功能酰亚胺催化一锅法亲电三氟甲基硫代-硫-Michael/aldol 级联反应，用于构建含 CFS 的螺环戊酮-硫色满。这种方便的一锅法级联反应为手性构建潜在生物活性螺环戊酮-硫色满提供了有力工具，该反应具有一个含 CFS 基团的季立体中心和三个连续的立体中心，包括一个螺全碳季立体中心，在中等至良好的收率下具有优异的立体选择性（高达 15:1 dr，>99%ee）。还实现了得到的产物的合成转化。
