过渡金属催化氧/氮杂环丙烷不对称开环反应的研究进展

doi:10.6023/cjoc202207034

有机化学 ›› 2022, Vol. 42 ›› Issue (10): 3240-3262.DOI: 10.6023/cjoc202207034 上一篇下一篇

所属专题：不对称催化专辑

综述与进展

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)

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摘要/Abstract

氧/氮杂环丙烷是一类重要的三元杂环结构, 由于三元环环张力较大, 因此具有较高的反应活性. 过渡金属催化下氧/氮杂环丙烷的不对称开环反应是一种高效构建含氧、氮杂原子手性分子的策略. 通过该策略可以构筑一系列手性醇、胺及相应杂环化合物. 综述了近二十年来过渡金属催化氧/氮杂环丙烷的不对称开环反应研究进展, 重点讨论了过渡金属催化剂、亲核试剂和配体的类型等因素对不对称开环反应的影响, 探讨了其反应机制及其在有机合成化学中的应用, 并对该领域的发展方向进行了展望.

关键词: 过渡金属催化, 氧杂环丙烷, 氮杂环丙烷, 不对称开环反应, 亲核偶联

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

引用此文

杜青锋, 张璐, 高峰, 王乐, 张万斌. 过渡金属催化氧/氮杂环丙烷不对称开环反应的研究进展[J]. 有机化学, 2022, 42(10): 3240-3262.

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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图/表 45

图式1. 过渡金属催化氧杂环丙烷和氮杂环丙烷的不对称开环反应及其应用

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

图式2. 过渡金属催化乙烯基氧/氮杂环丙烷的不对称烯丙基烷基化反应

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

图式3. 钯催化异戊二烯环氧化物与β-酮酯类化合物的不对称烯丙基烷基化反应

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

图式4. 钯催化异戊二烯环氧化物与芳基乙酸酯的不对称烯丙基烷基化反应

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

图式5. 钯催化乙烯基氮三元杂环与氨基羧酸酯的不对称烯丙基胺化反应

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

图式6. 钯催化环氧丁烯与磺酰二胺的不对称烯丙基胺化反应

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

图式7. 钯催化环氧丁烯与肼或羟胺的不对称烯丙基胺化反应

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

图式8. 钯催化环氧丁烯与琥珀酰胺阴离子的不对称烯丙基胺化反应

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

图式9. 钯催化剂催化乙烯基氮杂环丙烷与吲哚或吡咯的不对称烯丙基烷基化反应

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

图式10. 钯催化乙烯基环氧化物的分子内烯丙基胺化环化反应

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

图式11. 钯/Tunephos催化环氧丁烯与酰胺阴离子的不对称烯丙基烷基化反应

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

图式12. 乙烯基环氧化物的Pd-AAA-ICR反应

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

图式13. 钯催化乙烯基环氧化物与对甲氧基苄醇的不对称烯丙基化反应

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

图式14. Pd/NHC催化氮杂环丙烷与芳基硼酸的开环反应

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

图式15. 铑催化氮杂环丙烷与羟基芳烃的亲核开环反应

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

图式16. 铑催化氮杂环丙烷与吲哚的亲核开环反应

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

图式17. 铱催化乙烯基环氧化合物与伯醇的氧化还原诱导碳-碳键偶联反应

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

图式18. 铱催化乙烯基氮杂环丙烷与伯醇或醛的氧化还原诱导碳碳键偶联反应

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

图式19. 铱催化环氧化物与双胺的立体收敛性氧化还原亲核偶联反应

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

图式20. 钯催化乙烯基化合物与亚胺的不对称[3+2]环加成反应

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

图式21. 铑/银催化环氧丁烯与亚胺的不对称[3+2]环加成反应

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

图式22. 钯催化乙烯基环氧化物与对醌甲基化物的不对称环加成反应

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

图式23. 钯催化的乙烯基氮杂环丙烷与a,β-不饱和酮的不对称[3+2]环加成反应

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

图式24. 钯催化的乙烯基氮杂环丙烷与a,β-不饱和酮的不对称[3+2]环加成反应

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

图式25. 钯催化乙烯基环氧化合物与苯并杂环分子的不对称[3+2]环加成反应

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

图式26. 双金属协同催化乙烯基环氧化物与亲核偶极子的不对称[3+2]环加成反应

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

图式27. 铑催化乙烯基氮杂环丙烷与1,3-丁二烯类化合物的不对称[3+2]环加成反应

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

图式28. Salen-Co/胺双催化体系催化环氧化合物的不对称氟代反应

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

图式29. Salen-Co/钛双催化meso-氮杂环丙烷的不对称氟代反应

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

图式30. “头对尾”双金属Salen-Co催化meso-氧杂环丙烷的不对称开环偶联反应

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

图式31. 铜催化乙炔基环氧化物的不对称胺化反应

Scheme 31. Cu-catalyzed asymmetric amination of ethynyl epoxides

图式32. 镍催化3,4-环氧醇的不对称胺解反应

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

图式33. 铜催化氮杂环丙烷的不对称开环反应

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

图式34. 铜催化2-芳基-N-磺酰基氮杂环丙烷与吲哚的不对称Friedel-Crafts烷基化反应

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

图式35. 镍/钛双催化meso-环氧化物与芳基溴化物的不对称开环偶联反应

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

图式36. 镍催化3,4-环氧醇与芳基碘化物的不对称开环偶联反应

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

图式37. 镍催化氮杂环丙烷的对映选择性还原交叉偶联反应

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

图式38. 镍/光双催化氧/氮杂环丙烷与芳基碘化物的不对称开环偶联反应

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

图式39. 镍催化螺环环氧吲哚酮与烯基硼酸的不对称开环偶联反应

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

图式40. 钴催化螺环环氧吲哚酮与烯丙基硼的不对称开环偶联反应

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

图式41. 镍催化环氧乙烷与富电子化合物的不对称[3+2]环加成反应: 构建手性呋喃类化合物

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

图式42. 镍催化氮杂环丙烷的不对称[3+2]环加成反应

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

图式43. 铜催化氮杂环丙烷的不对称[3+2]环加成反应

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

图式44. 钪催化乙烯基环氧化物与不饱和亲电化合物的不对称Meinwald重排-插烯加成反应

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

图式45. 钪/铱双金属催化乙烯基环氧化物与烯丙醇的Meinwald重排-不对称烯丙基化反应

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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