Enantioselective Cycloaddition of in Situ Formed aza-Dienes and Vinyl Diazo Compounds for the Synthesis of Optically Enriched and Diazo Containing Tetrahydropyridazine.

Autor: Li SL; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China., Yang T; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China., Yin YX; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China., Karmaker PG; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China., Chu WD; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China., Zhou Q; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China., Liu QZ; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Dec 20; Vol. 89 (24), pp. 18752-18758. Date of Electronic Publication: 2024 Dec 10.
DOI: 10.1021/acs.joc.4c02499
Abstrakt: A copper catalyzed enantioselective formal aza-Diels-Alder reaction of in situ formed 1,2-diaza-1,3-dienes from α-halohydrazones and vinyl diazo compounds was described. The protocol provides a variety of optically enriched diazo-containing tetrahydropyridazines in moderate yields and with up to excellent enantioselectivities. The present methodologies utilize chiral oxazolines as the chiral ligands for asymmetric catalysis and feature mild reaction conditions, readily available substrates, and broad substrate scope.
Databáze: MEDLINE