手性双官能硫族化合物催化烯烃的不对称亲电硫化反应
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姜权彬博士, 2016年在中国科学院大连化学物理研究所获得有机化学博士学位, 导师余正坤研究员. 现在中山大学化学学院博士后流动站从事博士后研究, 合作导师赵晓丹教授. 研究方向为烯烃的亲电转化. |
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赵晓丹教授, 2007年底在中国科学院大连化学物理研究所有机化学专业博士毕业, 导师余正坤研究员, 期间作为交换学生在加拿大渥太华大学Howard Alper课题组学习和从事研究工作一年. 2008~2010年在多伦多大学从事博士后研究, 合作导师Vy M. Dong教授. 2010~2013年在美国科罗拉多州立大学Tomislav Rovis课题组从事博士后研究. 2013年入职中山大学化学学院, 开始独立科研工作. 研究方向为有机硫属化合物催化、不对称催化和有机氟化学. |
收稿日期: 2020-10-05
修回日期: 2020-11-03
网络出版日期: 2020-12-05
基金资助
国家自然科学基金(21901261); 国家自然科学基金(21772239); 中国博士后科学基金(2018M633207); 中央高校基本科研业务费(20lgzd21); 中央高校基本科研业务费(20lgpy81)
Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes
Received date: 2020-10-05
Revised date: 2020-11-03
Online published: 2020-12-05
Supported by
the National Natural Science Foundation of China(21901261); the National Natural Science Foundation of China(21772239); the China Postdoctoral Science Foundation(2018M633207); the Fundamental Research Funds for the Central Universities(20lgzd21); the Fundamental Research Funds for the Central Universities(20lgpy81)
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.
关键词： 有机催化; 手性双官能硒醚/硫醚催化; 不对称催化; 烯烃双官能团化; 手性硫化合物
姜权彬 , 赵晓丹 . 手性双官能硫族化合物催化烯烃的不对称亲电硫化反应[J]. 有机化学, 2021 , 41(2) : 443 -454 . DOI: 10.6023/cjoc202010005
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.
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