手性双官能硫族化合物催化烯烃的不对称亲电硫化反应

doi:10.6023/cjoc202010005

有机化学 ›› 2021, Vol. 41 ›› Issue (2): 443-454.DOI: 10.6023/cjoc202010005 上一篇下一篇

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手性双官能硫族化合物催化烯烃的不对称亲电硫化反应

姜权彬¹, 赵晓丹¹^,^*()

1 中山大学化学学院有机化学研究所和生物无机与合成化学教育部重点实验室广州 510275

收稿日期:2020-10-05 修回日期:2020-11-03 发布日期:2020-12-05
通讯作者: 赵晓丹

作者简介:

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.

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.

* Corresponding author. E-mail: zhaoxd3@mail.sysu.edu.cn

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

Quanbin Jiang¹, Xiaodan Zhao¹^,^*()

1 Institute of Organic Chemistry & Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education,School of Chemistry, Sun Yat-Sen University, Guangzhou 510275

Received:2020-10-05 Revised:2020-11-03 Published:2020-12-05
Contact: Xiaodan Zhao
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)

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摘要/Abstract

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

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.

Key words: organocatalysis, chiral bifunctional chalcogenide catalysis, asymmetric catalysis, alkene difunctionalization, chiral sulfide

引用此文

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.

Quanbin Jiang, Xiaodan Zhao. Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 443-454.

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图/表 23

图式1. 烯烃的不对称亲电硫化反应

Scheme 1. Enantioselective electrophilic thiolation of alkenes

图1. 基于(1,1'-联萘)-2,2'-二胺骨架的手性Lewis碱硒化磷酰胺催化剂

Figure 1. Chiral Lewis basic selenophosphoramide catalyst based on 1,1'-Binaphthyl-2,2'-diamine (BINAM) backbone

图式2. 手性硫鎓离子中间体消旋化方式

Scheme 2. Racemization pathways of chiral thiiranium ion intermediates

图式3. 手性双官能硒醚/硫醚催化剂绑定策略

Scheme 3. Binding strategy of chiral bifunctional chalcogenide catalyst

图式4. 合成手性双官能手性硒硫醚催化剂

Scheme 4. Synthesis of chiral bifunctional chalcogenide catalyst

图2. 手性双官能硒醚/硫醚催化剂

Figure 2. Chiral bifunctional chalcogenide catalyst

图式5. 单硒醚催化的烯烃三氟甲硫胺化反应

Scheme 5. Selenide catalyzed trifluoromethylthioamination of alkenes

图式6. 单硒醚催化的烯烃三氟甲硫胺化的反应机理

Scheme 6. Proposed mechanism of selenide catalyzed trifluoromethylthioamination of alkenes

图式7. 手性双官能硒醚/硫醚催化剂的筛选

Scheme 7. Screening of chiral bifunctional chalcogenide catalysts

图式8. 烯烃不对称三氟甲硫内酯化反应

Scheme 8. Enantioselective trifluoromethylthiolating lactonization of alkenes

图式9. 烯烃不对称三氟甲硫内酯化反应可能的机理

Scheme 9. Proposed mechanism of enantioselective trifluoromethylthiolating lactonization of alkenes

图式10. 条件筛选

Scheme 10. Screening of conditions

图式11. 烯烃不对称三氟甲硫胺化反应

Scheme 11. Enantioselective CF3S aminocyclization of alkenes

图式12. 手性硒醚催化的偕二芳基烯烃不对称三氟甲硫基化/去对称化反应

Scheme 12. Chiral selenide catalyzed enantioselective trifluoromethylthiolation/desymmetrization of gem-diaryl-tethered alkenes

图式13. 硒醚催化的N-烯丙基酰胺不对称三氟甲硫基化反应

Scheme 13. Selenide-catalyzed enantioselective trifluoromethylthiolation of N-allylamides

图式14. 手性硒醚催化的烯烃不对称烯丙基三氟甲硫基化反应

Scheme 14. Chiral selenide catalyzed enantioselective allylic trifluoromethylthiolation of alkenes

图式15. 烯烃分子间三氟甲硫基化官能团化反应

Scheme 15. Intermolecular enantioselective trifluoromethylthiolation of alkenes

图式16. 手性硒醚催化的烯烃不对称烯丙基化和分子间双官能化反应可能的途径

Scheme 16. Possible pathways of chiral selenide-catalyzed enantioselective allylic reaction and intermolecular difunctionalization of alkenes

图式17. 邻基协助的烯烃双官能化的机理假设

Scheme 17. Mechanistic hypothesis of difunctionalization of alkenes by neighboring group assistance

图式18. 脂肪族内烯烃高区域和对映选择性氧三氟甲硫基化反应

Scheme 18. Regio- and enantio-selective oxytrifluoromethylthiolation of aliphatic internal alkenes

图式19. 手性硒醚催化的N-烯丙基磺酰胺不对称烷硫基化反应

Scheme 19. Chiral selenide catalyzed enantioselective alkylthiolation of N-allyl sulfonamides

图式20. 不对称叠氮硫化反应的反应机理

Scheme 20. Proposed mechanism of enantioselective azidothiolation

图式21. 手性硒醚催化的N-烯丙基磺酰胺不对称芳硫基化反应

Scheme 21. Chiral selenide catalyzed enantioselective arylthiolation of N-allyl sulfonamides

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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

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