Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
A highly diastereo- and enantioselective Mannich reaction of isatin-derived ketimines with oxo-indanecarboxylates catalyzed by chiral thiourea derived from hydroquinidine has been developed. A series of 3-substituted 3-amino-oxindoles containing assembled bicyclic rings linked by a C-C bond were constructed by this protocol in excellent yields (92-99%) with high enantioselectivities (85-99% ee) and diastereoselectivities (up to >99 : 1 dr).
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8ob02595a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Asymmetric Organocatalytic [3 + 2]-Cycloaddition of -Alkoxy-4-oxo-acrylamides with Isatin-Derived Ketimines: Access to Enantioselective Synthesis of Spirooxindole-imidazolidinones.
Org Lett
May 2025
Department of Chemistry, Kyonggi University, Suwon-si 16227, Republic of Korea.
The spirooxindole framework is a privileged motif in numerous biologically significant natural products and has been demonstrated as a crucial core scaffold in a variety of medicinally significant compounds. Herein, we achieved a highly efficient enantioselective [3 + 2]-cycloaddition reaction of -alkoxy-4-oxo-acrylamides with isatin-derived ketimines. This method enabled the precise synthesis of chiral spirooxindole-imidazolidinone derivatives, which are notable for their intricate structures and the presence of chiral quaternary centers.
View Article and Find Full Text PDFAsymmetric [3+2] Cycloannulation of Benzoxazinones for the Synthesis of Imidazo[5,1-]oxazinones.
Org Lett
April 2025
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.
The asymmetric catalytic [3+2] cycloannulation of benzoxazinones with isatin-derived ketimines for the efficient construction of imidazo[5,1-]oxazinones has been developed, which realized the first asymmetric reaction of benzoxazinones with excellent stereoselectivities. A series of imidazo[5,1-]oxazinones containing three stereogenic centers with one -diamine-type spiro tetrasubstituted center were obtained in this organocatalytic reaction with good yields and high functional group tolerance.
View Article and Find Full Text PDFCopper(II)-Catalyzed Enantioselective Addition of Aryl Amines to Isatin-Derived -Boc-Ketimines for the Synthesis of Acyclic ,'-Ketals.
J Org Chem
January 2025
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, China.
Here, we demonstrated a copper(II)-catalyzed enantioselective addition of aryl amines to isatin-derived -Boc-ketimines using chiral O-N-N tridentate ligands derived from BINOL and proline. Generally, the chiral acyclic ,'-ketals were obtained in high yields (up to 98%) and excellent ee values (up to 98%). Various aryl amines could be tolerated and a gram-scale reaction was also possible.
View Article and Find Full Text PDFHighly Enantioselective Synthesis of Polycyclic Dihydroisoquinolinones via NHC-Catalyzed [4 + 2] Annulations.
J Org Chem
October 2024
College of Chemistry and Materials Science, Chemical Biology Key Laboratory of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Hebei University, Baoding 071002, China.
The NHC-catalyzed enantioselective [4 + 2] annulation of 9-fluorene-1-carbaldenydes with cyclic imines was successfully developed. A series of optically enriched polycyclic dihydroisoquinolinones were synthesized in moderate to excellent yields with good to excellent enantioselectivities. In addition, this efficient method could also be amenable to the synthesis of spirocyclic compounds by using isatin-derived ketimines as the electrophiles.
View Article and Find Full Text PDFEnantioselective Mannich Reaction between Cyclic -Sulfonyl Ketimines and Isatin-Derived Ketimines.
J Org Chem
September 2024
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.
Article Synopsis
- A new enantioselective Mannich reaction was created using cyclic -sulfonyl ketimines as nucleophiles with a chiral thiourea catalyst.
- The reaction produced high yields (84-99%) and impressive enantioselectivities (75-99.8% ee) when combined with isatin-derived ketimines.
- Preliminary tests showed that some resulting compounds effectively inhibited the growth of human osteosarcoma cells, indicating potential for anti-cancer applications.