过渡金属催化的烯/炔丙基杂原子偶极前体参与的不对称环化反应

doi:10.6023/cjoc202206028

摘要/Abstract

手性杂环化合物是一类重要的手性物质, 存在于许多手性药物、农药及催化剂中, 实现其催化不对称合成一直是有机合成的研究热点. 而过渡金属催化的杂原子偶极参与的不对称环化反应是构建该骨架的重要方法. 其中, 基于过渡金属催化的烯/炔丙基取代反应设计的杂原子偶极前体在近二十年来发展迅速, 在该领域占有着重要地位. 详细介绍了烯/炔丙基杂原子偶极前体参与的过渡金属催化不对称环化反应, 分析了目前方法的优势及存在的问题, 以期为从事催化不对称合成及相关领域的研究者提供有益借鉴和参考.

关键词: 过渡金属催化, 杂原子偶极, 不对称环化

Chiral heterocyclic compounds are an important class of chiral substances, which are widespread in many chiral drugs, pesticides and catalysts. Therefore, the efficient asymmetric synthesis of these compounds becomes a research hotspot in organic synthesis. Transition metal-catalyzed asymmetric cyclization with heteroatom-dipole precursors is an important method to construct these frameworks. Among them, the heteroatom-dipole precursors designed based on transition metal-catalyzed allyl or propargyl substitutions have been extensively studied in the past two decades and occupied an important role in this field. The transition metal-catalyzed asymmetric cyclizations with allyl or propargyl heteroatom-dipole precursors are introduced in detail. The advantages and existing problems of the current methods are analyzed, which would provide useful reference for the researchers in asymmetric synthesis and related fields.

Key words: transition metal catalysis, heteroatom dipole, asymmetric cyclization

引用此文

张键, 陈颖, 汪全南, 沈佳欢, 刘飏子, 邓卫平. 过渡金属催化的烯/炔丙基杂原子偶极前体参与的不对称环化反应[J]. 有机化学, 2022, 42(10): 3051-3101.

Jian Zhang, Ying Chen, Quannan Wang, Jiahuan Shen, Yangzi Liu, Weiping Deng. Transition Metal-Catalyzed Asymmetric Cyclizations Involving Allyl or Propargyl Heteroatom-Dipole Precursors[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3051-3101.

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图/表 119

图1. 常见的过渡金属稳定的杂原子偶极子

Figure 1. Common transition metal stabilized heteroatom dipoles

图式1. 烯/炔丙基杂原子偶极前体

Scheme 1. Alkenyl/propargyl heteroatom-dipole precursors

图式2. 首例钯催化的乙烯基氮丙啶参与的不对称环化反应

Scheme 2. The first Pd-catalyzed asymmetric cyclizations of vinyl aziridines

图式3. 氮杂环与乙烯基氮丙啶的不对称[3+3]环化反应合成哌嗪酮

Scheme 3. Asymmetric [3+3] cyclizations of nitrogen heterocycles with vinyl aziridines to piperazinones

图式4. 钯催化的乙烯基氮丙啶与α,β-不饱和酮的不对称[3+2]环化反应

Scheme 4. Pd-catalyzed asymmetric [3+2] cyclizations of vinyl aziridines with α,β-unsaturated ketones

图式5. 钯催化的乙烯基氮丙啶与亚甲基吲哚酮的不对称[3+2]环化反应

Scheme 5. Pd-catalyzed asymmetric [3+2] cyclizations of vinyl aziridines with methyleneindolones

图式6. 钯/仲胺协同催化的乙烯基氮丙啶与烯醛的不对称[3+2]环化反应

Scheme 6. Pd/Secondary amine co-catalyzed asymmetric [3+2] cyclizations of vinyl aziridines with enals

图式7. 乙烯基氮丙啶参与的催化不对称去芳构反应

Scheme 7. Catalytic asymmetric dearomatizations of vinyl aziridines

图式8. 钯催化的乙烯基氮丙啶与N-磺酰基亚胺的不对称[3+2]环化反应

Scheme 8. Pd-catalyzed asymmetric [3+2] cyclizations of vinyl aziridines with N-sulfonylimides

图式9. 钯催化的乙烯基氮丙啶与对醌衍生物的不对称[4+3]环化反应

Scheme 9. Pd-catalyzed asymmetric [4+3] cyclizations of vinylaziridines with para-quinone derivatives

图式10. 钯催化的乙烯基氮丙啶与茚满-1,3-二酮的不对称[3+2]环化反应

Scheme 10. Pd-catalyzed asymmetric [3+2] cyclizations of vinyl aziridines with indane-1,3-diones

图式11. 三催化剂共催化合成手性烯基吡咯烷酮

Scheme 11. Three-catalyst co-catalyzed synthesis of the chiral alkenyl pyrrolidone

图式12. 氮杂环卡宾/铱/脲催化[4+3]环化反应合成苯二氮?类和苯并噁氮?类化合物

Scheme 12. [4+3] cyclizations to access benzodiazepinones and benzoxazepinones via N-heterocyclic carbene (NHC)/Ir/urea catalysis

图式13. 首例钯催化烯基苯并噁嗪酮参与的不对称反应

Scheme 13. The first Pd-catalyzed asymmetric reactions of vinyl benzoxazinones

图式14. 钯催化的烯基苯并噁嗪酮与硫叶立德的不对称[4+1]环化反应

Scheme 14. Pd-catalyzed asymmetric [4+1] cyclizations of vinyl benzoxazinanones with sulphur ylides

图式15. 烯基苯并噁嗪酮与硫叶立德的不对称[4+1]环化反应机理

Scheme 15. Proposed mechanism of asymmetric [4+1] cyclizations of vinyl benzoxazinanones with sulphur ylides

图式16. 金属钯/胺协同催化的烯基苯并噁嗪酮与烯醛的不对称[4+2]环化

Scheme 16. Pd/Amine co-catalyzed asymmetric [4+2] cyclizations of vinyl benzoxazinanones with enals

图式17. 金属钯/氮杂环卡宾协同催化的烯基苯并噁嗪酮与烯醛的不对称[4+3]环化

Scheme 17. Pd/NHC co-catalyzed asymmetric [4+3] cyclizations of vinyl benzoxazinanones with enals

图式18. 烯基苯并噁嗪酮与烯醛的不对称[4+3]环化机理

Scheme 18. Proposed mechanism of asymmetric [4+3] cyclizations of vinyl benzoxazinanones with enals

图式19. 新型膦-硫配体参与的钯催化不对称[4+2]环化反应

Scheme 19. Pd-catalyzed asymmetric [4+2] cyclizations involving novel P,S-ligands

图式20. 可见光和钯接力催化的不对称[4+2]环化反应

Scheme 20. Sequential visible-light photoactivation and palladium catalysis enabling asymmetric [4+2] cyclizations

图式21. 钯催化的烯基苯并噁嗪酮与靛红衍生物的不对称环化反应

Scheme 21. Pd-catalyzed asymmetric cyclizations of vinyl benzoxazinanones with isatin derivatives

图式22. 钯催化的手性二氢喹唑啉酮的不对称合成

Scheme 22. Pd-catalyzed asymmetric synthesis of chiral dihydroquinazolinones

图式23. 钯催化的烯基苯并噁嗪酮与芳基乙酸的不对称环化反应

Scheme 23. Pd-catalyzed asymmetric cyclizations of vinyl benzoxazinanones with aryl acetic acids

图式24. 钯催化的烯基苯并噁嗪酮与环状亚胺的不对称[4+2]环化反应

Scheme 24. Pd-catalyzed asymmetric [4+2] cyclizations of vinyl benzoxazinanones with cyclic imines

图式25. 钯催化的烯基苯并噁嗪酮与环外烯烃的催化不对称环化反应

Scheme 25. Pd-catalyzed asymmetric cyclizations of vinyl benzoxazinanones with exo-cyclic olefins

图式26. 钯催化的烯基苯并噁嗪酮参与的吲哚不对称去芳构反应

Scheme 26. Pd-catalyzed asymmetric dearomatizations of indoles with vinyl benzoxazinanones

图式27. 反电子需求的钯催化不对称[4+2]环化反应

Scheme 27. Inverse-electron-demand Pd-catalyzed asymmetric [4+2] cyclizations

图式28. 钯催化的烯基苯并噁嗪酮与氮杂双烯区域选择性不对称环化反应

Scheme 28. Pd-catalyzed regioselective asymmetric cyclizations of vinyl benzoxazinanones with azadienes

图式29. 钯催化的不对称[4+2]环化反应合成手性螺吡唑酮

Scheme 29. Pd-catalyzed synthesis of chiral spiropyrazolones via [4+2] catalytic asymmetric cyclizations

图式30. 钯催化的1,2,4-苯并三氮杂?的不对称合成

Scheme 30. Pd-catalyzed asymmetric synthesis of 1,2,4-benzotriazepines

图式31. 钯催化的烯基苯并噁嗪酮的不对称分子内环化

Scheme 31. Pd-catalyzed asymmetric intramolecular cyclizations of vinyl benzoxazinanones

图式32. 铱/叔胺协同催化的手性吲哚螺环化合物的合成

Scheme 32. Synthesis of chiral indole spiro compounds catalyzed by Ir/tertiary amines co-catalysis

图式33. 钯催化的烯基噁嗪酮与光催化生成的烯酮化合物的不对称[8+2]环化反应

Scheme 33. Pd-catalyzed asymmetric [8+2] cyclizations of vinyl oxazinones with photogenerated ketenes

图式34. 钯催化的乙烯基噁唑烷酮与烯烃的不对称[3+2]环化反应

Scheme 34. Pd-catalyzed asymmetric [3+2] cyclizations of vinyl oxazolidinones with alkenes

图式35. 钯催化的乙烯基噁唑烷酮与磺酰亚胺的不对称[3+2]环化反应

Scheme 35. Pd-catalyzed asymmetric [3+2] cyclizations of vinyl oxazolidinones with sulfonyl imines

图式36. 乙烯基吲哚并噁唑酮参与的手性稠环吲哚化合物的区域发散性合成

Scheme 36. Regio-divergent asymmetric cyclizations of vinyl indolooxazolones

图式37. 乙烯基吲哚并噁唑酮与芳基乙酸酐[3+2]环化反应的机理

Scheme 37. Proposed mechanism for asymmetric [3+2] cyclizations of vinyl indolooxazolones with aryl acetic anhydrides

图式38. 烯基吲哚并噁唑酮与环状亚胺的区域发散性不对称环化反应

Scheme 38. Regio-divergent asymmetric cyclizations of vinyl indolooxazolones with cyclic imines

图式39. 钯催化的烯基碳酸亚乙酯与甲醛的不对称[3+2]环化反应

Scheme 39. Pd-Catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with formaldehyde

图式40. 钯催化的烯基碳酸亚乙酯与腈基取代的烯烃的不对称[3+2]环化反应

Scheme 40. Pd-Catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with nitrile substituted alkenes

图式41. 钯催化的烯基碳酸亚乙酯与异氰酸酯的不对称[3+2]环化反应

Scheme 41. Pd-Catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with isocyanates

图式42. 钯催化的烯基碳酸亚乙酯与亚胺的不对称[3+2]环化反应

Scheme 42. Pd-Catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with imines

图式43. 钯催化的烯基碳酸亚乙酯与3-氰基色酮的不对称 [3+2]环化反应

Scheme 43. Pd-catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with 3-cyanochromones

图式44. 钯络合物与方酰胺协同催化的烯基碳酸亚乙酯与β-硝基烯烃的不对称[3+2]环化反应

Scheme 44. Pd/Squaramide co-catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with β-nitroolefins

图式45. 钯催化的烯基碳酸亚乙酯与2-硝基丙烯酸酯的不对称[3+2]环化反应

Scheme 45. Palladium catalyzed asymmetric [3+2] cyclizations of vinylethylene carbonates with 2-nitroacrylates

图式46. 烯基碳酸亚乙酯与吡喃酮衍生物的不对称串联反应

Scheme 46. Asymmetric cascade reactions of vinyl ethylene carbonates with pyrone derivatives

图式47. 烯基碳酸亚乙酯与环状亚胺的催化不对称[3+2]环化反应

Scheme 47. Catalytic asymmetric [3+2] cyclizations of vinyl ethylene carbonates with cyclic imines

图式48. 烯基碳酸亚乙酯参与的手性呋喃螺吲哚骨架的构建

Scheme 48. Construction of chiral furanospiroindoles of vinyl ethylene carbonates

图式49. 铱/氮杂环卡宾协同催化不对称环化反应构建手性内酯

Scheme 49. Ir/NHC co-catalyzed asymmetric cyclizations for the construction of chiral lactones

图式50. 烯基碳酸亚乙酯和二氟烯烃的催化不对称环化反应

Scheme 50. Catalytic asymmetric cyclizations of vinyl ethylene carbonates with difluoroalkenes

图式51. 钯催化不对称环化构建多手性中心四氢呋喃化合物

Scheme 51. Pd-catalyzed asymmetric cyclizations for multistereogenic tetrahydrofurans

图式52. 钯/铑协同催化的不对称[3+2]环化反应

Scheme 52. Pd/Rh co-catalyzed asymmetric [3+2] cyclizations

图式53. 铱/铜双金属协同催化烯基碳酸亚乙酯与亚甲胺叶立德的不对称[3+2]环化反应

Scheme 53. Ir/Cu co-catalyzed asymmetric [3+2] cyclizations of vinyl ethylene carbonates with azomethine ylides

图式54. 烯基碳酸亚乙酯与靛红酸酐衍生物的不对称环化反应

Scheme 54. Asymmetric cyclizations of vinyl ethylene carbonates and isatoic anhydride derivatives

图式55. [3+2]环化/Cope重排串联反应合成环内联烯

Scheme 55. Synthesis of endocyclic allenes by [3+2] cyclization/Cope rearrangement cascade reactions

图式56. 多取代烯基碳酸亚乙酯与异氰酸酯和酮的[3+2]环化反应

Scheme 56. [3+2] Cyclizations of polysubstituted vinyl ethylene carbonates with isocyanates or ketones

图式57. 烯基碳酸亚乙酯参与的手性九元环骨架的构建

Scheme 57. Construction of chiral nine-membered rings involving vinyl ethylene carbonates

图式58. 协同催化的烯基碳酸亚乙酯与烯醛的不对称环化反应

Scheme 58. Co-catalyzed asymmetric cyclizations of vinyl ethylene carbonates with enals

图式59. 钯与卡宾协同催化的不对称[5+2]环化反应

Scheme 59. Pd/NHC co-catalyzed asymmetric [5+2] cyclizations

图式60. 可见光/钯接力催化的不对称[5+2]环化反应

Scheme 60. Sequential visible-light photoactivation and palladium catalysis enabling asymmetric [5+2] cyclizations

图式61. 烯基碳酸亚乙酯参与的手性八元环的构建

Scheme 61. Construction of chiral eight-membered rings involving vinyl ethylene carbonates

图式62. 烯基碳酸亚乙酯与苯并亚胺磺酸酯的不对称[5+2]环化反应

Scheme 62. Asymmetric [5+2] cyclizations of vinyl ethylene carbonates with benzimide sulfonates

图式63. 烯基碳酸亚乙酯与氧杂双烯的催化不对称[5+4]环化反应

Scheme 63. Catalytic asymmetric [5+4] cyclizations of vinyl ethylene carbonates with oxadienes

图式64. 烯基碳酸亚乙酯与苯并噁嗪酮的催化不对称环化反应

Scheme 64. Catalytic asymmetric cyclizations of vinyl ethylene carbonates with benzoxazinones

图式65. 烯基碳酸亚乙酯与烯炔酰胺的催化不对称[5+4]环化反应

Scheme 65. Catalytic asymmetric [5+4] cyclizations of vinyl ethylene carbonates with enynamides

图式66. 首例钯催化乙烯基环氧乙烷参与的不对称环化反应报道

Scheme 66. The first report of Pd-catalyzed asymmetric cyclizations of vinyloxiranes

图式67. 天然产物(-)-Acosamine的全合成

Scheme 67. Total synthesis of natural product (-)-Acosamine

图式68. 钯催化的乙烯基环氧乙烷与异氰酸酯(碳二亚胺)的不对称环化反应

Scheme 68. Pd-Catalyzed asymmetric cyclizations of vinyloxiranes with isocyanates (carbodiimides)

图式69. 钯或者镍催化的乙烯基环氧乙烷与亚胺的不对称环化反应

Scheme 69. Pd- or Ni-catalyzed asymmetric cyclizations of vinyloxiranes with imines

图式70. 铑催化的乙烯基环氧乙烷与亚胺衍生物的不对称 [3+2]环化反应

Scheme 70. Rh-catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with imine derivatives

图式71. 钯催化的乙烯基环氧乙烷与硝基烯烃的不对称[3+2]环化反应

Scheme 71. Pd-catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with nitroalkenes

图式72. 钯催化的乙烯基环氧乙烷与对醌亚甲基化物的不对称[3+2]环化反应

Scheme 72. Pd-catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with para-quinone methylates

图式73. 钯催化的乙烯基环氧乙烷与α,β-不饱和酮的不对称[3+2]环化反应

Scheme 73. Pd-catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with α,β-unsaturated ketones

图式74. 钯催化乙烯基环氧乙烷参与的不对称去芳构化反应

Scheme 74. Pd-catalyzed asymmetric dearomatizations with vinyloxiranes

图式75. 钯催化的乙烯基环氧乙烷与多取代硝基烯烃的催化不对称环化反应

Scheme 75. Pd-catalyzed asymmetric cyclizations of vinyloxiranes with polysubstituted nitroalkenes

图式76. 钯催化的乙烯基环氧乙烷与联烯酰胺的不对称[3+2]环化反应

Scheme 76. Pd-catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with allenic amides

图式77. 钯催化的不对称环化反应合成手性异核苷类似物

Scheme 77. Synthesis of chiral isonucleoside analogues by Pd-catalyzed asymmetric cyclizations

图式78. 钯催化的乙烯基环氧乙烷与N-苯并噻唑亚胺的不对称[3+2]环化反应

Scheme 78. Pd-Catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with N-benzothiazolimines

图式79. 钯催化的乙烯基环氧乙烷与氮杂双烯的不对称[3+2]环化反应

Scheme 79. Pd-Catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with azadienes

图式80. 手性螺环化合物的立体发散性合成

Scheme 80. Stereo-divergent synthesis of chiral spiro componds

图式81. 螺环产物作为氮-烯配体应用于铑催化的不对称反应

Scheme 81. Rh-catalyzed asymmetric additions using the spiro product as the N-olefin ligand

图式82. 钯催化的乙烯基环氧乙烷与活化炔烃的不对称[3+2]环化反应

Scheme 82. Pd-catalyzed asymmetric [3+2] cyclizations of vinyloxiranes with activated alkynes

图式83. 镍/氮杂环卡宾协同催化的不对称[3+3]环化反应

Scheme 83. Ni/NHC co-catalyzed asymmetric [3+3] cyclizations

图式84. 亚甲基二噁烷酮参与的催化不对称环化反应

Scheme 84. Catalytic asymmetric cyclizations of methylenedioxanones

图式85. 可见光诱导的亚甲基二噁烷酮的不对称环化反应

Scheme 85. Visible light-induced asymmetric cyclizations of methylenedioxanones

图式86. 亚甲基二噁唑烷酮与MBH碳酸酯的不对称[4+3]环化反应

Scheme 86. Asymmetric [4+3] cyclizations of methylenedioxanones with MBH carbonates

图式87. 烯基二噁唑烷酮与MBH碳酸酯的不对称[4+3]环化反应

Scheme 87. Asymmetric [4+3] cyclizations of methylenedioxanones with MBH carbonates

图式88. 化合物276a的立体发散性合成

Scheme 88. Stereodivergent synthesis of the product 276a

图式89. 手性环状和非环状的偕二氟亚甲基化合物的合成

Scheme 89. Synthesis of chiral cyclic and acyclic gem-difluoromethylenes

图式90. 烯基二噁烷酮与甲醛的催化不对称[4+2]环化反应

Scheme 90. Catalytic asymmetric [4+2] cyclizations of alken- yldioxanones with formaldehyde

图式91. 烯基二噁烷酮与硝基烯烃的催化不对称[4+2]环化反应

Scheme 91. Catalytic asymmetric [4+2] cyclizations of alken- yldioxanones with nitroalkenes

图式92. 首例钯催化乙烯基噁丁环参与的不对称反应

Scheme 92. The first case of Pd-catalyzed asymmetric reactions of vinyl oxetanes

图式93. 钯催化的乙烯基噁丁环与甲醛的不对称[4+2]环化反应

Scheme 93. Pd-catalyzed asymmetric cyclizations of vinyl oxetanes with formaldehyde

图式94. 三醇化合物的不对称合成

Scheme 94. Asymmetric synthesis of the triol compound

图式95. 吲哚稠环的不对称合成

Scheme 95. Asymmetric synthesis of indole fused rings

图式96. 乙烯基氨基醇和醛或β,γ-不饱和酮的不对称[4+2]环化反应

Scheme 96. Asymmetric [4+2] cyclizations of vinyl aminoalcohols and aldehydes or β,γ-unsaturated ketones

图式97. 铱催化不对称烯基化/扩环反应构建苯并八元杂环

Scheme 97. Iridium-catalyzed asymmetric allylation/ring expansion reactions to construct benzo heterocyclic rings

图式98. 铱/金催化的不对称环化反应合成螺缩酮和螺缩醛胺化合物

Scheme 98. Iridium/gold catalyzed asymmetric cyclizations for synthesis of spiroketals and spiroaminals

图式99. 氮杂烯丙基碳酸酯与异氰酸酯的催化不对称环化反应

Scheme 99. Catalytic asymmetric cyclizations of aza-allyl carbonates and isocyanates

图式100. 铱/氮杂环卡宾协同催化的区域/立体发散性不对称[3+2]/[3+3]环化反应

Scheme 100. Ir/NHC co-catalyzed regio/stereodivergent asymmetric [3+2]/[3+3] cyclizations

图式101. 配体控制的钯催化区域选择性[4+2]/[4+4]环化反应

Scheme 101. Ligand-controlled, palladium-catalyzed regio-selectively asymmetric [4+2]/[4+4] cyclizations

图式102. 乙烯基硫杂环丙烷与杂聚烯的催化不对称环化反应

Scheme 102. Catalytic asymmetric cyclizations of 2-vinylthi- iranes and heterocumulenes

图式103. 铜催化乙炔基苯并噁嗪酮与硫叶立德的催化不对称[4+1]环化反应

Scheme 103. Cu-catalyzed asymmetric [4+1] cyclizations of ethynyl benzoxazinones with sulfur ylides

图式104. 钯催化的乙炔基苯并噁嗪酮与吲哚的不对称[4+2]环化反应

Scheme 104. Pd-catalyzed asymmetric [4+2] cyclizations of ethynyl benzoxazinones with indoles

图式105. 协同催化的乙炔基苯并噁嗪酮与芳基乙酸的不对称环化反应

Scheme 105. Co-catalyzed asymmetric cyclizations of ethynyl benzoxazinones with arylacetic acids

图式106. 铜催化的乙炔基苯并噁嗪酮与硅烷氧基呋喃的不对称[4+2]环化反应

Scheme 106. Cu-catalyzed asymmetric [4+2] cyclizations of ethynyl benzoxazinones with silyloxyfurans

图式107. 铜催化的乙炔基苯并噁嗪酮与六氢-1,3,5-三嗪的不对称环化反应

Scheme 107. Cu-catalyzed asymmetric cyclizations of ethynyl benzoxazinones with hexahydro-1,3,5-triazines

图式108. 铜催化的乙炔基苯并噁嗪酮与亚甲胺亚胺的不对称环化反应

Scheme 108. Cu-catalyzed asymmetric cyclizations of ethynyl benzoxazinones with azomethine imines

图式109. 协同催化的乙炔基苯并噁嗪酮与吖内酯的不对称[4+2]环化反应

Scheme 109. Co-catalyzed asymmetric [4+2] cyclizations of ethynyl benzoxazinones with azlactones

图式110. 铜催化的乙炔基苯并噁嗪酮与吖内酯的不对称[4+2]环化反应

Scheme 110. Cu-catalyzed asymmetric [4+2] cyclizations of ethynyl benzoxazinones with azlactones

图式111. 协同催化的炔基苯并噁嗪酮与烯醛的不对称[4+3]环化反应

Scheme 111. Co-catalyzed asymmetric [4+3] cyclizations of ethynyl benzoxazinones with enals

图式112. 炔基噁唑酮与丙二腈的催化不对称[3+2]环化反应

Scheme 112. Catalytic asymmetric [3+2] cyclizations of ethy- nyl oxazolidinone with malononitrile

图式113. 乙炔基噁唑酮与γ-丁烯内酯的催化不对称[3+2]环化反应

Scheme 113. Catalytic asymmetric [3+2] cyclizations of ethy- nyl oxazolidinones with γ-butenolides

图式114. 铜催化的炔基吲哚并噁唑酮与吖内酯的不对称[3+2]环化反应

Scheme 114. Cu-catalyzed asymmetric [3+2] cyclizations of ethynyl indolooxazolidones with azlactones

图式115. 炔基吲哚并噁唑酮与芳基乙酸的催化不对称环化反应

Scheme 115. Catalytic asymmetric cyclizations of ethynyl indoloxazolidones with aryl acetic acids

图式116. 协同催化的乙炔基碳酸亚乙酯与丙二腈的不对称 [3+2]环化反应

Scheme 116. Co-catalyzed asymmetric [3+2] cyclizations of ethynyl ethylene carbonates with malononitriles

图式117. 协同催化的乙炔基碳酸亚乙酯与烯醛的不对称[4+3]环化反应

Scheme 117. Co-catalyzed asymmetric [4+3] cyclizations of ethynyl ethylene carbonates with enals

图式118. 炔基碳酸亚乙酯与吖内酯的催化不对称[3+2]环化反应

Scheme 118. Catalytic asymmetric [3+2] cyclizations of ethy- nyl ethylene carbonates with azlactones

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