Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes

doi:10.6023/cjoc202010005

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 443-454.DOI: 10.6023/cjoc202010005 Previous Articles Next Articles

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ACCOUNT

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)

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

Cite this article

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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Fig. & Tab. 23

Scheme 1. Enantioselective electrophilic thiolation of alkenes

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

Scheme 2. Racemization pathways of chiral thiiranium ion intermediates

Scheme 3. Binding strategy of chiral bifunctional chalcogenide catalyst

Scheme 4. Synthesis of chiral bifunctional chalcogenide catalyst

Figure 2. Chiral bifunctional chalcogenide catalyst

Scheme 5. Selenide catalyzed trifluoromethylthioamination of alkenes

Scheme 6. Proposed mechanism of selenide catalyzed trifluoromethylthioamination of alkenes

Scheme 7. Screening of chiral bifunctional chalcogenide catalysts

Scheme 8. Enantioselective trifluoromethylthiolating lactonization of alkenes

Scheme 9. Proposed mechanism of enantioselective trifluoromethylthiolating lactonization of alkenes

Scheme 10. Screening of conditions

Scheme 11. Enantioselective CF3S aminocyclization of alkenes

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

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

Scheme 14. Chiral selenide catalyzed enantioselective allylic trifluoromethylthiolation of alkenes

Scheme 15. Intermolecular enantioselective trifluoromethylthiolation of alkenes

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

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

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

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

Scheme 20. Proposed mechanism of enantioselective azidothiolation

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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