A mild and efficient enantioselective amination of 4-alkylisoquinoline-1,3(2,4)-dione derivatives was established, which is compatible with a broad range of substrates and delivers the final products in excellent yields (up to 99%) and ee values (up to 99%) with low catalyst loading (down to 1 mol%). The synthetic potential of this methodology was also demonstrated in the gram scale level.
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http://dx.doi.org/10.1039/d0ra07806a | DOI Listing |
Angew Chem Int Ed Engl
January 2025
IISER Kolkata: Indian Institute of Science Education and Research Kolkata, Department of Chemical Sciences, Mohanpur, 741246, Nadia, INDIA.
Chiral allyl amines are important structural components in natural products, pharmaceuticals, and chiral catalysts. Herein, we report a cobalt-catalyzed enantioselective reductive coupling of imines with internal alkynes to synthesize chiral allyl amines. The reaction is catalyzed by a cobalt complex derived from commercially available bisphosphine ligand utilizing zinc as the electron donor.
View Article and Find Full Text PDFChirality
January 2025
Department of Chemistry, Shyam Lal College, University of Delhi, New Delhi, India.
Enantiomeric analysis of chiral drugs is very significant, as their enantiomers display different pharmacological or toxicological behavior towards living systems. Among these drugs, β-blockers are available as racemates, where their enantiomers display different pharmacological effects. Herein, we report enantioselective separation of two β-blockers, namely, atenolol and sotalol, using a derivatization approach.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, United States.
The utilization of β-fluoroamines as pharmaceutical components for drug development has attracted a considerable amount of interest. However, direct access to tertiary β-fluoroamines is challenging. We herein report the rhodium-catalyzed asymmetric amination of tertiary allylic trichloroacetimidates with anilines and cyclic aliphatic amines to access tertiary β-fluoroamines, where the α-carbon atom is bonded to four different substituents, in good yield with high levels of enantioselectivity.
View Article and Find Full Text PDFJ 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 PDFJ Am Chem Soc
January 2025
Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.
Catalytic enantioselective substitution of the readily available racemic α-halo carbonyl compounds by nitrogen nucleophiles represents one of the most convenient and direct approaches to access enantioenriched α-amino carbonyl compounds. Distinct from the two available strategies involving radicals and enolate ions, herein we have developed a new protocol featuring an electronically opposite way to weaken/cleave the carbon-halogen bond. A suitable chiral anion-based catalyst enables effective asymmetric control over the key positively charged intermediates.
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