International Cooperative Laboratory of Traditional Chinese Medicine Moderniza-tion and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, China.
Chem Commun (Camb). 2020 Aug 11;56(62):8842-8845. doi: 10.1039/d0cc02876b. Epub 2020 Jul 7.
Highly enantio- and diastereoselective phosphine-catalyzed [3+2] cycloadditions of terminal allenoates with β-perfluoroalkyl α,β-enones leading to a range of trifluoromethylated cyclopentenes with two contiguous chiral centers (up to 99% yield with 99% ee) have been developed. Moreover, these reactions could be performed at the gram scale by using only 1 mol% catalyst. The method developed here was also applied to the concise synthesis of trifluoromethylated DGAT-1 inhibitor.
手性膦催化末端烯丙酯与β-全氟烷基-α,β-烯酮的高对映选择性和非对映选择性[3+2]环加成反应，得到一系列具有两个连续手性中心的三氟甲基环戊烯（高达 99%的收率和 99%的对映体过量）。此外，这些反应可以在克级规模下进行，只需使用 1 mol%的催化剂。这里开发的方法也被应用于三氟甲基化 DGAT-1 抑制剂的简洁合成。
