不对称有机催化MBH碳酸酯与噻唑基烯酮的[1+4]环化反应构建含有噻唑骨架的手性二氢呋喃衍生物

Asymmetric Organocatalytic Enantioselective[1+4]-Annulation of Morita-Baylis-Hillman Carbonates with Thiazolyl Enones for Assembling of Dihydrofurans Featuring Thiazole Skeleton

发展了一种手性有机膦催化的Morita-Baylis-Hillman(MBH)碳酸酯与1-芳基-3-(5-噻唑基)-2-丙烯-1-酮的不对称[1+4]环化反应,用于不对称合成含有噻唑骨架的手性二氢呋喃衍生物.该反应的产率为49%~96%,对映选择性(e.e.)为92%~99%,非对映选择性(d.r.)从6∶1至高于20∶1.该研究拓展了手性有机膦催化体系的应用范围,同时为高效构建含有噻唑和二氢呋喃2种结构单元的手性杂环化合物提供了良好的催化策略.

The phosphine catalyzed enantioselective[1+4]-annulation of 1-aryl-3-(thiazol-5-yl)prop-2-enone with Morita-Baylis-Hillman carbonate was developed,which enabled the formation of structurally diversified 2,3-dihydrofurans featuring thiazole skeleton in yields of 49%—96%with e.e.of 92%—99%and d.r.from 6∶1 to more than 20∶1.Notably,this work extended the application range of the established catalytic system and provided an excess to the chiral complex heterocyclic compounds containing dihydrofuran and thiazole structural units.