Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds

doi:10.6023/cjoc202308012

Abstract

Enantioenriched C—N axial chiral compounds are ubiquitous in many important field, such as natural products, chiral drugs and chiral ligands. Therefore, efficient construction of C—N axis chirality through asymmetric catalytic synthesis has attracted more and more attention and research interest. In this review, the recent progress in asymmetric synthesis of C—N axis chiral compounds has been discussed, mainly from three aspects: desymmetrization of prochiral molecules or kinetic resolution of racemates, atroposelective functionalization of C—N axis, and atroposelective C—N coupling reaction. The topic focuses on the evolution of asymmetric catalytic system and the key factors of chiral control. The existing problems and future development direction of this field are also discussed. This paper is a timely and systematic review and will stimulate more extensive research interest.

Key words: C—N axis chiral compounds, desymmetrization, asymmetric catalysis, atroposelective

Cite this article

Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.

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Fig. & Tab. 64

Scheme 1. Enantioenriched C—N axial chiral compounds and asymmetric catalytic strategies

Scheme 2. Desymmetrization of N-aryl maleimide

Scheme 3. Rh-catalyzed asymmetric 1,4-addition of N-aryl maleimide

Scheme 4. Rh-catalyzed asymmetric hydroarylation of N-aryl maleimide

Scheme 5. Rh-catalyzed asymmetric carboamination of norbornene derivative

Scheme 6. Ni-catalyzed asymmetric hydronitridation of norbornene derivative

Scheme 7. Pd-catalyzed asymmetric hydrosilylation of N-aryl maleimide

Scheme 8. Ag-catalyzed asymmetric 1,3-dipolar cycloaddition

Scheme 9. Addition/cycloaddition of N-aryl maleimide

Scheme 10. Desymmetrization of N-aryl maleimide via Michal addition

Scheme 11. Sc-catalyzed desymmetrization of N-aryl maleimide via Michal addition

Scheme 12. NHC-catalyzed desymmetrization of N-aryl maleimide

Scheme 13. NHC-catalyzed desymmetrization of N-aryl urease

Scheme 14. Desymmetrization of 4-aryl-1,2,4-triazole-3,5-dione

Scheme 15. Desymmetrization of 1,2,4-triazole-3,5-dione via ene reaction

Scheme 16. Synthesis of of axial chiral N-arylpyrroles

Scheme 17. Pd-catalyzed debromination hydrogenation desymmetrization

Scheme 18. Chiral peptide-catalyzed atroposelective bromination

Scheme 19. Chiral phosphoric acid-catalyzed atroposelective electrophilic bromination

Scheme 20. Atroposelective Pictet-Spengler reaction

Scheme 21. NHC-catalyzed kinetic resolution of anilides

Scheme 22. Synthesis of atropisomeric anilides through enantioselective N-allylation

Scheme 23. Asymmetric N-allylation catalyzed by double quinine organic bases

Scheme 24. N-Allylation reaction of phosphamides catalyzed by hydroxyquinine

Scheme 25. Pd-catalyzed asymmetric N-arylation/acylation of amides

Scheme 26. Chiral thiourea catalyzed atroposelective N-acylation

Scheme 27. Chiral phase transfer catalyzed asymmetric N-alkylation

Scheme 28. Pd-catalyzed asymmetric C—H functionalization

Scheme 29. Chiral auxiliary group-directed asymmetric C—H alkylation

Scheme 30. Chiral auxiliary group-directed asymmetric C—H olefination

Scheme 31. Pd-catalyzed amine-directed asymmetric C—H olefination

Scheme 32. Rh-catalyzed construction of axial chirality and central chirality via asymmetric carboamidation

Scheme 33. Pd-catalyzed atroposelective C—N coupling

Scheme 34. Cu-catalyzed atroposelective C—N coupling

Scheme 35. Pd-catalyzed atroposelective Catellani reaction/carbonyl insertion reaction

Scheme 36. Atroposelective aza-cycloaddition reaction of alkynes

Scheme 37. Chiral guanidine-catalyzed tandem isomerization/ Michael reactions of alkynes

Scheme 38. Photocatalytic synthesis of N—C axial chiral heterocycles

Scheme 39. Chiral phosphoric acid catalyzed atroposelective intramolecular acylation reaction

Scheme 40. Rh-catalyzed asymmetric C—H activation/acetylene insertion annulation

Scheme 41. Rh-catalyzed C—H activation and atroposelective annulation

Scheme 42. Co/Salox-catalyzed asymmetric C—H activation/annulation

Scheme 43. Chiral phosphoric acid catalyzed atroposelective Paal-Knorr reaction

Scheme 44. Chiral phosphoric acid catalyzed atroposelective nitrogen annulation

Scheme 45. Construction of axial chiral N-arylbenzimidazole via intramolecular condensation

Scheme 46. Enantioselective synthesis of N-aryl benzimidazoles

Scheme 47. Atroposelective synthesis of isoindolinones

Scheme 48. Enantioselective synthesis of N-aryl quinazolinones

Scheme 49. NHC-catalyzed atroposelective annulation to thiazine derivatives

Scheme 50. NHC-catalyzed atroposelective [3＋4] annulation

Scheme 51. Atroposelective synthesis of N-aryl naphthoimidazole

Scheme 52. Rh-catalyzed atroposelective [2＋2＋2] cycloaddition

Scheme 53. Rh-catalyzed asymmetric C—H activation/cyclization reaction of N-aryl indolinone

Scheme 54. Rh-catalyzed asymmetric C—H activation/ynamine insertion annulation

Scheme 55. Rh-catalyzed atroposelective Click reaction

Scheme 56. Rh-catalyzed atroposelective [2＋2＋2] cycloaddition with ynamide

Scheme 57. Enantiopure sulfinyl iodanes induced Cu-catalyzed atroposelective aryl amination

Scheme 58. Cu-catalyzed asymmetric C—N coupling reaction

Scheme 59. Ir-catalyzed atroposelective synthesis of enamides

Scheme 60. Chiral phosphoric acid-catalyzed asymmetric electrophilic amination

Scheme 61. Atroposelective amination of arenes

Scheme 62. Atroposelective synthesis of 3-amino indole

Scheme 63. Atroposelective synthesis of N-arylated quinoids

Scheme 64. Rh-catalyzed atroposelective N—H insertion of carbene

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C—N轴手性化合物的不对称催化合成研究进展