Copper(II)-Catalyzed Enantioselective Addition of Aryl Amines to Isatin-Derived N-Boc-Ketimines for the Synthesis of Acyclic N,N′-Ketals DOI

Leipeng Xue,

Jiahui Li,

Tianxu Yu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 90(1), С. 75 - 85

Опубликована: Дек. 31, 2024

Here, we demonstrated a copper(II)-catalyzed enantioselective addition of aryl amines to isatin-derived N-Boc-ketimines using chiral O–N–N tridentate ligands derived from BINOL and proline. Generally, the acyclic N,N′-ketals were obtained in high yields (up 98%) excellent ee values 98%). Various could be tolerated gram-scale reaction was also possible. Further, an X-ray diffraction experiment confirmed that configuration N-Boc ketimine should (Z). Confirmation would make it easier understand rationale for stereofacial selective activation electrophile with either organo- or Lewis acid–based catalysts.

Язык: Английский

Cu(II)‐Catalyzed Enantioselective Aza‐Friedel‐Crafts Reaction of 1‐Naphthols and Electron‐Rich Phenols with Isatin‐Derived Ketimines DOI

Qihang Cai,

Tianxu Yu,

Jiahui Li

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(27)

Опубликована: Март 4, 2024

New chiral ligands could be obtained by introducing proline moieties and imidazoline to binaphthyl skeletons. The exhibited balanced rigidity flexibility which allow the change of conformations during reactions on one hand, provide sufficient asymmetric induction other. moiety act as a linker connecting skeletons well coordinating group for central metal, electronic steric properties groups carefully fine-tuned use different substituents. In presence Cu(II) catalyst bearing such ligands, aza-Friedel-Crafts reaction 1-naphthols electron-rich phenols with isatin-derived ketimines provided desired products good excellent yields up 99 % ee. showed scalability, ee still when was carried out in gram-scale.

Язык: Английский

Процитировано

3
Baker’s yeast bio-catalyzed green and efficient synthesis of 3-indolylmethanamine via Aza-Friedel Crafts Reaction of indole with imines DOI Creative Commons

Samreen Kausar,

Qasim Ullah,

Mohammed Arifuddin

и другие.

Discover Chemistry., Год журнала: 2025, Номер 2(1)

Опубликована: Апрель 16, 2025

Язык: Английский

Процитировано

0
Development and characterization of an aluminum-enhanced graphene oxide nanocomposite: An Eco-friendly and sustainable catalyst for electrochemical Friedel-crafts reactions DOI
Amjad Ali, Dheyaa J. Jasim,

Nodir Rakhimov

и другие.

Journal of Molecular Structure, Год журнала: 2024, Номер 1319, С. 139373 - 139373

Опубликована: Июль 26, 2024

Язык: Английский

Процитировано

2
Copper(II)-Catalyzed Enantioselective Addition of Aryl Amines to Isatin-Derived N-Boc-Ketimines for the Synthesis of Acyclic N,N′-Ketals DOI

Leipeng Xue,

Jiahui Li,

Tianxu Yu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 90(1), С. 75 - 85

Опубликована: Дек. 31, 2024

Here, we demonstrated a copper(II)-catalyzed enantioselective addition of aryl amines to isatin-derived N-Boc-ketimines using chiral O–N–N tridentate ligands derived from BINOL and proline. Generally, the acyclic N,N′-ketals were obtained in high yields (up 98%) excellent ee values 98%). Various could be tolerated gram-scale reaction was also possible. Further, an X-ray diffraction experiment confirmed that configuration N-Boc ketimine should (Z). Confirmation would make it easier understand rationale for stereofacial selective activation electrophile with either organo- or Lewis acid–based catalysts.

Язык: Английский

Процитировано

0