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Relevant academic research and scientific papers

Synthesis of a novel sterically hindered chiral cyclic phosphoric acid derived from L-tartaric acid and application to the asymmetric catalytic Biginelli reaction

A novel sterically hindered chiral cyclic phosphoric acid derived from L-tartaric acid was designed and synthesized based on highly regioselective cyclosulfitation of chiral 1,1,4,4-tetraphenylbutanetetraol. The asymmetric Biginelli reaction catalyzed by

Highly enantioselective Biginelli reaction catalyzed by double axially chiral bisphosphorylimides

Double axially chiral bisphosphorylimides have been used as catalysts in enantioselective Biginelli reactions. The three-component reaction of aromatic aldehydes, thiourea, and ethyl acetoacetate took place by using 5 mol-% catalyst in ethyl acetate at 50°C. A series of chiral dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 97 %) with good to high enantioselectivities (up to 96 % ee) in only 12 hours. The three-component Biginelli reaction was catalyzed by BINOL-derived double axially chiral bis-phosphorylimides. The catalyst with 3,3′-2-naphthyl substituents most effectively catalyzed the reaction and a series of chiral dihydropyrimidinethiones (DHPMs) were obtained in high yields up to 97 % with 90-96 % ee in only 12 hours. Copyright

Highly Enantioselective Biginelli Reaction Catalyzed by Double Axially Chiral Bisphosphorylimides

Double axially chiral bisphosphorylimides have been used as catalysts in enantioselective Biginelli reactions. The three-component reaction of aromatic aldehydes, thiourea, and ethyl acetoacetate took place by using 5 mol-% catalyst in ethyl acetate at 50 C. A series of chiral dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 97 %) with good to high enantioselectivities (up to 96 % ee) in only 12 hours.

Highly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids

A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to excellent enantioselectivities (up to 99% ee). The synthetic utility of this method was demonstrated by the synthesis of chiral precursors of three drugs, including (S)-Monastrol, (S)-L-771688 and (S)-SQ 32926.

Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: Reversal of the stereochemistry by tuning the 3,3′-disubstituents of phosphoric acids

Organocatalytic enantioselective Biginelli and Biginelli-like reactions by chiral phosphoric acids derived from 3,3′-disubstituted binaphthols have been investigated. The size of 3,3′-substituents of the catalysts is able to control the stereochemistry of