Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines

doi:10.6023/cjoc202207034

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3240-3262.DOI: 10.6023/cjoc202207034 Previous Articles Next Articles

Special Issue: 不对称催化专辑

REVIEWS

过渡金属催化氧/氮杂环丙烷不对称开环反应的研究进展

杜青锋^a, 张璐^b, 高峰^b^,^*(), 王乐^a^,^*(), 张万斌^b

a 上海工程技术大学化学化工学院上海 201620
b 上海交通大学化学化工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

收稿日期:2022-07-26 修回日期:2022-08-18 发布日期:2022-11-02
通讯作者: 高峰, 王乐
作者简介:
†共同第一作者.
基金资助:
国家自然科学基金(21991112)

Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines

Qingfeng Du^a, Lu Zhang^b, Feng Gao^b(), Le Wang^a(), Wanbin Zhang^b

a School of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
b Shanghai Key Laboratory for Molecular Engineering and Chiral Drugs, Frontiers Science Center for Transformative Molecules Shanghai, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2022-07-26 Revised:2022-08-18 Published:2022-11-02
Contact: Feng Gao, Le Wang
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21991112)

Epoxides and aziridines are important three-membered cyclic compounds, which exhibit high reactivity due to their strong strain in molecules. The asymmetric ring-opening reactions of epoxides and aziridines catalyzed by transition metals are efficient strategies for the construction of chiral molecules containing O/N atoms. In this way, a series of chiral alcohols, chiral amines and chiral heterocycles can be constructed. The recent progress in transition metal-catalyzed asymmetric ring-opening reactions of epoxides and aziridines in the past two decades is reviewed with emphasis on the influence of the kinds of transition metal catalysts, nucleophiles, and ligands. Furthermore, the possible reaction mechanisms and applications for the asymmetric ring-opening reactions are discussed, and the future development in this field is also prospected.

Key words: transition metals catalysis, epoxide, aziridine, asymmetric ring-opening reaction, nucleophilic coupling

Cite this article

Qingfeng Du, Lu Zhang, Feng Gao, Le Wang, Wanbin Zhang. Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3240-3262.

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Fig. & Tab. 45

Scheme 1. Transition metal-catalyzed asymmetric ring-opening reactions of epoxides and aziridines and their applications

Scheme 2. Transition metal-catalyzed asymmetric allylic alkylation of vinyl epoxides and vinyl aziridines

Scheme 3. Pd-catalyzed asymmetric allylic alkylation of isoprene epoxides with β-ketoesters

Scheme 4. Pd-catalyzed asymmetric allylic alkylation of isoprene monoxide with arylacetates

Scheme 5. Pd-catalyzed asymmetric allylic amination of vinyl three-membered heterocyclic rings with imido carboxylates

Scheme 6. Pd-catalyzed asymmetric allylic amination of butadiene monoepoxide with sulfonyl diamine

Scheme 7. Pd-catalyzed asymmetric allylic amination of butadiene monoepoxide with hydrazines or hydroxylamines

Scheme 8. Pd-catalyzed asymmetric allylic amination of butadiene monoepoxide with succinimide

Scheme 9. Pd-catalyzed asymmetric allylic alkylation of vinyl aziridines with indoles or pyrroles

Scheme 10. Pd-catalyzed intramolecular allylic amination cyclization of vinyl epoxides

Scheme 11. Pd/Tunephos-catalyzed asymmetric allylic alkylation reaction of epoxybutene with amide anions

Scheme 12. Pd-AAA-ICR reaction of vinyl epoxides

Scheme 13. Pd-catalyzed asymmetric allylic alkylation of vinyl epoxide with p-methoxybenzyl alcohol

Scheme 14. Pd/NHC-catalyzed ring-opening reaction of aziridines with arylboronic acids

Scheme 15. Rh-catalyzed nucleophilic ring-opening reaction of hadroxyarenes with vinyl aziridines

Scheme 16. Rh-catalyzed nucleophilic ring-opening reaction of aziridines with indoles

Scheme 17. Ir-catalyzed redox-triggered C—C coupling reactions of vinyl epoxides with primary alcohols

Scheme 18. Ir-catalyzed redox-triggered C-C coupling reactions of vinyl aziridines with primary alcohols or aldehydes

Scheme 19. Ir-catalyzed stereoconvergent redox-neutral nucleophilic coupling reactions of epoxides with diamines

Scheme 20. Pd-catalyzed asymmetric [3+2] cycloaddition of vinyl epoxides with imine

Scheme 21. Rh/Ag-catalyzed [3+2] cycloaddition of vinyl epoxides and imines

Scheme 22. Pd-catalyzed asymmetric [3+2] cycloaddition of para-quinone methides with vinyl epoxides

Scheme 23. Pd-catalyzed asymmetric [3+2] cycloaddition of vinyl aziridines and a,β-unsaturated ketones

Scheme 24. Pd-catalyzed asymmetric [3+2] cycloaddition of vinyl epoxides and a,β-unsaturated ketones

Scheme 25. Pd-catalyzed asymmetric [3+2] cycloaddition of vinyl epoxides to benzoheterocycles

Scheme 26. Dual-metal-catalyzed asymmetric [3+2] cycladdition of vinyl epoxides with nucleophilic dipoles

Scheme 27. Rh-catalyzed asymmetric [3+2] cycloaddition of vinyl aziridines with 1,3-butadienes

Scheme 28. Salen-Co/amine dual-catalyzed asymmetric fluorination of epoxides

Scheme 29. Salen-Co/Ti dual-catalyzed asymmetric fluorination of meso-aziridines

Scheme 30. "Head-to-tail" bimetallic Salen-Co-catalyzed asymmetric ring-opening coupling reaction of meso-epoxides

Scheme 31. Cu-catalyzed asymmetric amination of ethynyl epoxides

Scheme 32. Ni-catalyzed asymmetric amination of 3,4-epoxy alcohols

Scheme 33. Cu-catalyzed asymmetric ring-opening coupling reactions of aziridines

Scheme 34. Cu-catalyzed asymmetric Friedel-Crafts alkylation of indoles with 2-Aryl-N-sulfonylaziridines

Scheme 35. Ni/Ti dual-catalyzed asymmetric ring-opening coupling reactions of meso-epoxides with aryl bromides

Scheme 36. Ni-catalyzed asymmetric ring-opening coupling reaction of 3,4-epoxy alcohols with aryl iodides

Scheme 37. Ni-catalyzed enantioselective reductive cross-coupling of aziridines

Scheme 38. Ni/PC dual-catalyzed asymmetric ring-opening coupling reactions of epoxides(aziridines) with aryl iodides

Scheme 39. Ni-catalyzed asymmetric ring-opening coupling reactions of spiro-epoxyoxindoles with alkenylboronic acids

Scheme 40. Co-catalyzed asymmetric ring opening reactions of spiro-epoxyoxindoles with allylboron

Scheme 41. Ni-catalyzed asymmetric [3+2] cycloaddition of epoxides with electron-rich compounds: construction of chiral furan derivative

Scheme 42. Ni-catalyzed asymmetric [3+2] cycloaddition of aziridines

Scheme 43. Cu-catalyzed asymmetric [3+2] cycloaddition of aziridines

Scheme 44. Sc-catalyzed asymmetric Meinwald rearrangement-vinylogous addition reactions of vinyl epoxides with unsaturated electrophilic compounds

Scheme 45. Sc/Ir dual-catalyzed asymmetric Meinwald rearrangement-asymmetric allylic alkylation of vinyl epoxides with allylic alcohols

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过渡金属催化氧/氮杂环丙烷不对称开环反应的研究进展

Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines

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