Key Laboratory of State Forestry and Grassland Administration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China, College of Material and Chemical Engineering, Southwest Forestry University, Kunming 650224, China.
Academy of Advanced Carbon Conversion Technology, Huaqiao University, Xiamen 361021, Fujian, China.
J Org Chem. 2023 Jun 2;88(11):7454-7462. doi: 10.1021/acs.joc.3c00006. Epub 2023 May 23.
Asymmetric addition of terminal alkynes catalyzed by a transition metal to isatins obviously is an efficient and economic method for the synthesis of 3-alkynyl-3-hydroxy-2-oxindoles. The new dimeric chiral quaternary ammoniums derived from a natural chiral alkaloid, quinine, can be used as cationic inducers of the enantioselectivity for the Ag(I)-catalyzed alkynylation of isatin derivatives under mild conditions. The desired chiral 3-alkynyl-3-hydroxy-2-oxindoles can be obtained in good to high yields with high to excellent enantioselectivites (≤99% ee). A variety of aryl-substituted terminal alkynes and substituted isatins are tolerated in this reaction.
手性双齿季铵盐的合成及其在不对称催化反应中的应用。手性双齿季铵盐是一类重要的有机小分子催化剂，具有良好的稳定性和对映选择性。本文以天然手性生物碱奎宁为原料，通过亲核取代反应合成了一系列新型的手性双齿季铵盐，并将其应用于不对称催化反应中。结果表明，这些手性双齿季铵盐能够有效地诱导不对称催化反应，提高反应的对映选择性。
