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

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 90(1), P. 75 - 85

Published: Dec. 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.

Language: 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

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(27)

Published: March 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.

Language: Английский

Citations

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

et al.

Discover Chemistry., Journal Year: 2025, Volume and Issue: 2(1)

Published: April 16, 2025

Language: Английский

Citations

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

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1319, P. 139373 - 139373

Published: July 26, 2024

Language: Английский

Citations

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

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 90(1), P. 75 - 85

Published: Dec. 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.

Language: Английский

Citations

0