手性双官能硫族化合物催化烯烃的不对称亲电硫化反应

Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes

手性含硫化合物在药物化学和不对称合成领域中应用广泛,发展这类化合物的新合成方法是有机合成化学的重要任务.烯烃的不对称亲电硫化反应为手性含硫化合物的合成提供了一条方便的途径,通过这种方式不仅可以在烯烃母体分子上引入一个含硫基团,同时也能够引入另外一个重要的官能团.我们课题组设计、合成了一系列手性双官能硒醚/硫醚催化剂,并成功将其应用在不同种类烯烃的分子内和分子间的不对称三氟甲硫基化、烷硫基化和芳硫基化反应,高对映选择性地合成了各种手性含硫化合物.总结了我们课题组在手性双官能硒醚/硫醚催化的烯烃不对称亲电硫化反应中的研究进展,并对该领域的发展进行展望.

Chiral organosulfur compounds have a wide range of applications in the fields of medicinal chemistry and asymmetric synthesis.The development of new methods for the preparation of these compounds is an important task in organic synthetic chemistry.Enantioselective electrophilic thiolation of alkenes has emerged as a straightforward pathway for the synthesis of chiral sulfides.By this fashion,both the thio group and another valuable functional group can be introduced simultaneously into the parent alkene molecules.We designed and synthesized a series of chiral bifunctional chalcogenide catalysts and successfully applied them to intra-and inter-molecular enantioselective trifluoromethylthiolation,alkylthiolation,arylthiolation of different kinds of alkenes.A variety of chiral sulfides were obtained with high enantioselectivities.The recent advances in chiral bifunctional chalcogenide catalyzed enantioselective thiofunctionalization of alkenes developed by our group are summarized,and the prospect of this field is also discussed.