Development of Earth-Abundant Metals-Catalyzed Enantioselective Alkenylations Using Alkenyl Metal Reagents

doi:10.6023/A21070338

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (11): 1331-1344.DOI: 10.6023/A21070338 Previous Articles Next Articles

Review

丰产金属催化烯基金属试剂的不对称烯基化反应研究进展

吴良^a, 魏瀚林^a, 申杰峰^a^,^*(), 陈建中^b^,^*(), 张万斌^a^,^b

a 上海交通大学药学院变革性分子前沿科学中心上海市手性药物分子工程重点实验室上海 200240
b 上海交通大学化学化工学院上海 200240

投稿日期:2021-07-20 发布日期:2021-09-17
通讯作者: 申杰峰, 陈建中

作者简介:

吴良, 2020年在上海交通大学获得博士学位(导师: 张万斌教授). 目前在上海交通大学张万斌教授课题组从事博士后研究工作, 主要研究方向为丰产金属催化的不对称反应.

申杰峰, 博士, 上海交通大学药学院副研究员, 硕士研究生导师. 2012博士毕业于上海交通大学化学化工学院(导师: 张万斌教授); 同年进入上海交通大学药学院从事博士后研究工作(导师: 刘燕刚教授). 2014年至今就职于上海交通大学药学院, 主要研究方向为不对称催化、化学工艺及新药开发研究.

陈建中, 上海交通大学化学化工学院副研究员. 本科毕业于浙江工业大学; 硕士毕业于华东理工大学(导师: 赵敏副教授); 博士毕业于上海交通大学(导师: 张万斌教授), 同年本校从事博士后研究(导师: 颜德岳院士). 自2015年起在上海交通大学主要从事不对称反应研究, 新型配体的设计、合成及应用, 药物和香料等合成工艺研究等.

基金资助:
上海市“超级博士后”激励计划(2020272); 国家自然科学基金(21620102003); 国家自然科学基金(21772119); 国家自然科学基金(21831005)

Development of Earth-Abundant Metals-Catalyzed Enantioselective Alkenylations Using Alkenyl Metal Reagents

Liang Wu^a, Hanlin Wei^a, Jiefeng Shen^a(), Jianzhong Chen^b(), Wanbin Zhang^a^,^b

a Shanghai Key Laboratory for Molecular Engineering and Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China
b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Received:2021-07-20 Published:2021-09-17
Contact: Jiefeng Shen, Jianzhong Chen
Supported by:
Shanghai Post-Doctoral Excellence Program(2020272); National Natural Science Foundation of China(21620102003); National Natural Science Foundation of China(21772119); National Natural Science Foundation of China(21831005)

Allylic chiral centers are widely present in natural products and pharmaceutically active molecules, and play a vital role in the construction of organic compounds through pericyclic reactions, oxidations or reductions and other transformations. The transition metal-catalyzed asymmetric addition or coupling reaction using alkenyl metal nucleophiles is one of the most attractive strategies for the synthesis of these structures. Among the many metal catalysts, earth-abundant transition metals such as iron, cobalt, nickel and copper have been used to replace precious metals such as rhodium and palladium, and have gained attention for use in enantioselective alkenylations. Indeed, remarkable advances have been achieved with these catalysts due to their unique catalytic activity, low toxicity and environmentally friendliness. The earth-abundant transition metals are known to undergo facile one electron oxidation state changes. In the reaction process, the earth-abundant transition metals have the ability to undergo two-electron transfer and single-electron transfer processes, therefore they have more valence changes and catalytic pathways which can be exploited. Based on this, this article will review the latest research in earth-abundant metal-catalyzed enantioselective alkenylation using alkenyl metal reagents. It is divided into four sections consisting of cobalt-catalyzed enantioselective alkenylations using alkenyl metal reagents, nickel-catalyzed enantioselective alkenylations using alkenyl metal reagents, copper-catalyzed enantioselective alkenylations using alkenyl metal reagents, and other earth-abundant transition metals catalyzed enantioselective alkenylations using alkenyl metal reagents.

Key words: earth-abundant metal catalysis, alkenyl metal reagent, enantioselective alkenylation, asymmetric addition, asymmetric coupling

Cite this article

Liang Wu, Hanlin Wei, Jiefeng Shen, Jianzhong Chen, Wanbin Zhang. Development of Earth-Abundant Metals-Catalyzed Enantioselective Alkenylations Using Alkenyl Metal Reagents[J]. Acta Chimica Sinica, 2021, 79(11): 1331-1344.

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Fig. & Tab. 38

Figure 1. Earth-abundant metals-catalyzed enantioselective alkenylation using alkenyl metal nucleophiles

Figure 2. Chiral allyl alcohols

Figure 3. Co-catalyzed asymmetric alkenylation of ketones and imines

Figure 4. Co-catalyzed asymmetric alkenylation of cyclopropenes

Figure 5. Co-catalyzed asymmetric coupling of α-bromo esters with alkenyl magnesium reagents

Figure 6. Chiral allyl amines

Figure 7. Ni-catalyzed asymmetric addition of cyclic aldimines with alkenyl boron reagents

Figure 8. Ni-catalyzed asymmetric addition of cyclic ketimines with alkenyl boron reagents

Figure 9. Proposed mechanism for ring-expansion step

Figure 10. Ni/Spiro aminophosphine catalyzed asymmetric alkenylation of styrenes

Figure 11. Ni/BOX catalyzed asymmetric alkenylation of styrenes

Figure 12. Ni-catalyzed asymmetric addition of aldehydes with alkenyl boron reagents and mechanism

Figure 13. Ni-catalyzed asymmetric coupling of α-bromo esters with alkenyl silicon reagents

Figure 14. Ni-catalyzed asymmetric coupling of α-bromo esters with alkenyl zirconium reagents

Figure 15. Ni-catalyzed asymmetric coupling of α-bromonitriles with alkenyl zinc reagents

Figure 16. Ni-catalyzed asymmetric coupling of α-bromosulfonamides with alkenyl zirconium reagents

Figure 17. Ni-catalyzed asymmetric coupling of spiro-epoxyoxindoles with alkenylboronic acids and mechanism

Figure 18. Ni-catalyzed asymmetric coupling of tertiary alkyl halides with alkenyl zirconium reagents

Figure 19. Mechanism studies

Figure 20. Cu-catalyzed asymmetric addition of aldehydes with alkenyl silicon reagents

Figure 21. Cu-catalyzed asymmetric addition of aldehydes with alkenyl boron reagents and mechanism

Figure 22. Cu-catalyzed asymmetric addition of trifluoromethyl ketones with alkenyl silicon reagents

Figure 23. Cu-catalyzed asymmetric addition of oxindoles with alkenyl silicon reagents

Figure 24. Cu-catalyzed asymmetric addition of cyclic enone with alkenyl aluminum reagents

Figure 25. Cu-catalyzed asymmetric addition of α,β-unsaturated cyclic ketones with alkenyl aluminum reagents

Figure 26. Cu-catalyzed asymmetric addition of cyclic enone with Si-containing alkenyl aluminum reagents

Figure 27. Cu-catalyzed asymmetric addition of cyclopropenes with alkenyl aluminum reagents

Figure 28. Cu-catalyzed asymmetric addition of α,β-unsaturated compounds with alkenyl boron reagents and mechanism

Figure 29. Cu-catalyzed asymmetric addition of α,β-unsaturated compounds with alkenyl aluminum reagents

Figure 30. Soft vs hard nucleophiles

Figure 31. Cu-catalyzed asymmetric coupling of allylic phosphates with alkenyl aluminum reagents

Figure 32. Cu-catalyzed asymmetric coupling of trisubstituted allylic phosphates with alkenyl aluminum reagents

Figure 33. Cu-catalyzed asymmetric coupling of allylic phosphates with Si-containing alkenyl aluminum reagents

Figure 34. Cu-catalyzed asymmetric coupling of trisubstituted allylic phosphates with alkenyl boron reagents

Figure 35. Cu-catalyzed asymmetric coupling of allylic phosphates with alkenyl boron reagents

Figure 36. Zn-catalyzed asymmetric addition of aldimines with alkenyl zirconium reagents and mechanism

Figure 37. Fe-catalyzed asymmetric coupling of α-chloroesters with alkenyl magnesium reagents and mechanism

Figure 38. Sc-catalyzed asymmetric addition of aldehydes with alkenyl silicon reagents

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丰产金属催化烯基金属试剂的不对称烯基化反应研究进展

Development of Earth-Abundant Metals-Catalyzed Enantioselective Alkenylations Using Alkenyl Metal Reagents

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