Efficient synthesis of biflavones having a ring-A ring of two flavone units using Suzuki cross-coupling reactions

Biflavones having a A ring-A ring of two flavone units were easily prepared by using Suzuki cross-coupling reaction of borylated flavones with bromoflavones or flavone-5-triflate in good to excellent yields

Efficient transformation of flav-3-enes using reductive elimination of flav-4-triflate

Flav-3-enes were prepared in excellent yields (up to 98%) by reductive elimination of flav-3-ene-4-triflates in the presence of palladium acetate, formic acid and tri-n-buthylamine

Chiral primary amino alcohol organobase catalyst for the asymmetric Diels-Alder reaction of anthrones with maleimides

Simple chiral TES-amino alcohol organocatalysts containing a bulkysilyl [triethylsilyl: TES] group on oxygen atom at γ-position were designed andsynthesized as new organocatalysts for the enantioselective Diels-Alder (DA) reactionof anthrones with maleimides to produce chiral hydroanthracene DA adducts (up to99% yield with up to 94% ee)

Lipase-catalyzed domino Michael-aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone for the synthesis of bicyclic compounds

Synthesis of bicyclic compounds was achieved via a lipase-catalyzed, stereoselective, domino Michael–aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone. Appropriate reaction conditions, including the type of enzyme, solvent, and temperature, were determined. In addition, the effects of solvent polarity and addtives were investigated. The reaction proceeded in the presence of lipase AS in a solution of 20% acetone in dimethylsulfoxide (DMSO) at 10 °C for 8 days, followed by the addition of p-toluenesulfonic acid (TsOH) to afford bicyclic compounds in 51–83% yields with moderate stereoselectivity. Although this domino Michael–aldol reaction showed only moderate stereoselectivity, even with the acid-supported enhancement of the reaction, these results represent potential new applications for lipase

A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine

Enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a novel chiral oxazolidine organocatalyst afforded chiral isoquinuclidines that is an efficient synthetic intermediate of oseltamivir, with fairly good chemical yield and excellent enantioselectivity (90%, up to >99% ee)

Tripeptide-Catalyzed Asymmetric Aldol Reaction Between α-ketoesters and Acetone Under Acidic Cocatalyst-Free Conditions

Here, we report the tripeptide-catalyzed asymmetric aldol reaction between α-ketoesters and acetone under acidic cocatalysts-free conditions. H-Pro-Tle-Gly-OH 3g-catalyzed reactions between α-ketoesters and acetone resulted in up to 95% yield and 88% ee. Analysis of the transition state using density functional theory (DFT) calculations revealed that the tert-butyl group in 3g played an important role in enantioselectivity