Advances on Chiral Phosphoric Acid Catalyzed Asymmetric Electrophilic Amination Reactions

doi:10.6023/cjoc202409028

Abstract

The catalytic enantioselective electrophilic amination reaction has emerged as a highly efficient method for synthesizing diverse nitrogen-containing chiral molecules, with the development of various asymmetric catalysis systems. Chiral phosphoric acids (CPA) have been widely acknowledged as versatile chiral organocatalysts since it was first discovered in 2004, finding application in catalyzing diverse asymmetric reactions. A comprehensive overview of recent advances in CPA-catalyzed asymmetric electrophilic amination reactions using different N-electrophilic reagents, including azo reagents, aryldiazonium salts, and imine derivatives, is presented. Furthermore, insights into future developments in this field are offered.

Key words: chiral phosphoric acid, electrophilic amination, azodicarboxylate, asymmetric catalysis, organocatalysis

Cite this article

Mengyao Tang, Xiaoyu Yang. Advances on Chiral Phosphoric Acid Catalyzed Asymmetric Electrophilic Amination Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1785-1818.

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Fig. & Tab. 42

Figure 1. Chiral amines and their asymmetric synthesis through catalytic enantioselective electrophilic amination reaction

Figure 2. CPA catalyst with various chiral scaffolds

Scheme 1. Chiral calcium phosphate-catalyzed enantioselective electrophilic amination of enamides

Scheme 2. CPA catalyzed enantioselective three-component amination of enecarbamates

Scheme 3. Enantioselective synthesis of 1,2-diamines catalyzed by chiral photosensitive organocatalysts

Scheme 4. CPA-catalyzed asymmetric amination of α‑branched cyclic ketones

Scheme 5. Chiral calcium phosphate-catalyzed enantioselective amination of 3-aryl-2-benzofuranones, 3-aryl-2-oxindoles and cyclic β-keto esters

Scheme 6. CPA-catalyzed enantioselective amination of acyclic branched α-alkynyl ketones and α-branched acyclic ynones

Scheme 7. Enantioselective synthesis of pyrroloindolines through CPA-catalyzed electrophilic amination

Scheme 8. Enantioselective synthesis of aza-quaternary carbon-containing indolenines via CPA-catalyzed aminative dearomatization

Scheme 9. CPA-catalyzed asymmetric dearomatization of indoles with azodicarboxylates via cascade electrophilic amination/aza-Prins cyclization/phenonium-like rearrangement

Scheme 10. CPA-catalyzed asymmetric dearomative azo-Diels-Alder reaction of 2-vinlyindoles

Scheme 11. Enantioselective synthesis of axially chiral urazoles via CPA-catalyzed electrophilic amination reaction of indoles

Scheme 12. Asymmetric synthesis of axially chiral naphthyl-indoles via CPA-catalyzed electrophilic amination

Scheme 13. Atroposelective synthesis of 3-aryl-indoles through a CPA-catalyzed one-pot 2,3-difunctionalization of indoles

Scheme 14. CADA of β-naphthols through CPA-catalyzed electrophilic amination with azodicarboxylates

Scheme 15. CPA aminative dearomatization/Michael addition sequence of α-naphthols

Scheme 16. CPA-catalyzed asymmetric amination for the construction of axially chiral urazoles embedded naphthalenones

Scheme 17. CPA catalyzed aminative dearomatization of substituted phenols

Scheme 18. Kinetic resolution of racemic BINOLs via CPA-catalyzed asymmetric amination with azodicarboxylates

Scheme 19. CPA-catalyzed remote control of axial chirality at carbon-boron bond with electrophilic amination

Scheme 20. KR of α,α-disubstituted hydroquinolines through CPA-catalyzed asymmetric aminations with azodicarboxylates

Scheme 21. KR of acyclic α-tertiary amines via CPA-catalyzed asymmetric aminations of arylamines

Scheme 22. KR of N-aryl β-amino alcohols and 1,2-diamines via CPA-catalyzed asymmetric electrophilic amination

Scheme 23. (Parallel) Kinetic resolution of 3,3-disubstituted indolines via CPA-catalyzed amination with azodicarboxylates

Scheme 24. Enantioselective desymmetrization of 1,3-propanediamines via CPA-catalyzed amination of anilines

Scheme 25. Remote enantioselective desymmetrization of 9,9-disubstituted 9,10-dihydroacridines through CPA-catalyzed amination

Scheme 26. Asymmetric synthesis of biaryl atropoisomers via CPA-catalyzed para-aminations arylamines

Scheme 27. Kinetic resolution of protecting-group-free BINAMs and NOBINs via CPA-catalyzed triazane formation

Scheme 28. Atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through CPA-catalyzed enantioselective C—H amination

Scheme 29. Atroposelective synthesis of nonbiaryl N-C atropisomers with stable configuration via CPA-catalyzed enantioselective amination

Scheme 30. Catalytic asymmetric synthesis of axially chiral diaryl ethers through aminative enantioselective desymmetrization

Scheme 31. Atroposelective synthesis of axially chiral diarylamines via CPA-catalyzed electrophilic amination

Scheme 32. Enantioselective synthesis of planar-chiral macrocycles via CPA-catalyzed electrophilic aromatic amination

Scheme 33. Kinetic resolution of substituted amido[2.2] paracyclophanes via CPA-catalyzed electrophilic amination

Scheme 34. Kinetic resolution of inherently chiral saddle-shaped eight-membered azaheterocycles via CPA-catalyzed asymmetric amination

Scheme 35. CAPT catalyzed enantioselective electrophilic amination of tryptamines and cyclic β-keto esters with aryldiazonium salts

Scheme 36. Catalytic enantioselective synthesis of C-N atropoisomers via CPA-catalyzed amination of indoles with p-quinone diimines via 1,6-addition

Scheme 37. Atroposelective synthesis of 2-arylindoles via CPA-catalyzed direct amination of indoles with QDIs

Scheme 38. Asymmetric dearomatization of 2,3-disubstituted indoles via CPA catalyzed 1,6-addition of QDIs

Scheme 39. CPA-catalyzed catalytic asymmetric dearomative [4＋2] cycloaddition of indoles with o-QDI

Scheme 40. CPA-catalyzed aromatization-promoted umpolung reaction of imines

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