A highly diastereoselective and enantioselective method for the asymmetric desymmetrization of 4,4-disubstituted cyclohexadienones using the Michael addition reaction of malonates under catalysis with the primary amine–thiourea conjugate catalyst and PPY at high pressure was developed.

A practical method for the synthesis of 1,3-aminohydroxyacetone synthons was developed, and their utility in the organocatalytic asymmetric aldol reaction was demonstrated in a short synthesis of aza-sugars.

A new environmentally friendly method for the Baeyer–Villiger oxidation of cyclobutanones has been developed. The reaction can be performed at room temperature by using thioureas as catalysts and H2O2 as the oxidant in toluene, and the desired γ-butyrolactone compounds are obtained in high yields.

A new method for chiral diamine-catalyzed Robinson-type annulation was developed to construct cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position in high enantiomeric excess. This method was successfully applied to the short synthesis of (+)-sporochnol A.

A new class of artificial anthracene-fused chiral proline catalysts has been synthesized from the Diels–Alder adduct of anthracene and maleic anhydride via lithiation/carboxylation of 6 as a key step. Chiral resolution of racemic amino acids was carried out through the formation of diastereomeric esters with (−)-menthol. The absolute configuration of the chiral amino acid was determined by X-ray crystallographic analysis. The utility of the catalyst was confirmed by effecting asymmetric three-component Mannich reactions between aldehyde, ketone, and amine (yield up to 76%, ee up to 90%).(1S,3aR,9aS)-4,9[1′,2′]Benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole-1-carboxylic acid (−)-menthyl esterC29H35NO2[α]D22 = +20.9 (c 1.62, MeOH)Source of chirality: diastereomeric ester resolutionAbsolute configuration: (1S,3aR,9aS)(1R,3aS,9aR)-4,9[1′,2′]Benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole-1-carboxylic acid (−)-menthyl esterC29H35NO2[α]D22 = −93.1 (c 1.41, MeOH)Source of chirality: diastereomeric ester resolutionAbsolute configuration: (1R,3aS,9aR)(1S,3aR,9aS)-4,9[1′,2′]Benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole-1-carboxylic acidC19H17NO2[α]D22 = +57.6 (c 0.62, MeOH)Source of chirality: diastereomeric ester resolutionAbsolute configuration: (1S,3aR,9aS)

A highly diastereoselective and enantioselective method for the asymmetric desymmetrization of 4,4-disubstituted cyclohexadienones using the Michael addition reaction of malonates under catalysis with the primary amine–thiourea conjugate catalyst and PPY at high pressure was developed.

A practical method for the synthesis of 1,3-aminohydroxyacetone synthons was developed, and their utility in the organocatalytic asymmetric aldol reaction was demonstrated in a short synthesis of aza-sugars.