ABSTRACT
Herein we report a catalytic asymmetric inverse-electron-demand Diels-Alder reaction between alkylidene pyrazolones and allyl ketones. Allyl ketone gets activated by a bifunctional thiourea catalyst and acts as a dienolate in this reaction. The trisubstituted tetrahydropyrano[2,3-c]pyrazoles were obtained in moderate to good yields with high diastereo- and enantioselectivities. Few applications, including a decarbonylation reaction, have been demonstrated.
Subject(s)
Pyrazolones , Pyrazoles , Ketones , Electrons , Cycloaddition Reaction , Molecular Structure , StereoisomerismABSTRACT
Intermolecular cross Rauhut-Currier reactions have gained much importance in recent years. It has proved its importance through procedures involving various catalysts and resulting in complex structures with good regio- as well as stereo- selectivity. This review highlights the recent developments of these reactions, published in current years, involving both achiral and chiral catalysts to give products, having various utilities. In addition, the detailed mechanistic studies of the above-mentioned reactions are also presented.
Subject(s)
Molecular Structure , Stereoisomerism , CatalysisABSTRACT
Herein, we employ unsaturated pyrazolones in the Rauhut-Currier reaction for the first time. A domino Rauhut-Currier cyclization reaction has been developed between unsaturated pyrazolones and nitro-olefins. The trisubstituted tetrahydropyrano[2,3-c]pyrazoles were obtained in moderate to high yields with excellent diastereoselectivities. A few applications including a synthesis of disubstituted tetrahydropyrano[2,3-c]pyrazole have been demonstrated. A preliminary catalytic asymmetric version of this process was also studied with chiral DMAP catalysts.
ABSTRACT
An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between (E)-2-(2-nitrovinyl)phenols and 1,3-propanediones is disclosed. A cinchona alkaloid derived bifunctional thiourea catalyst was found to be the most effective for this reaction and provided the desired products in moderate to good yields with good to high enantioselectivities.
