Abstract: The present invention presents a catalyst that allows asymmetric hydroxymethylation reactions to progress with excellent asymmetric selectivity and a production method for optically active hydroxymethylated compounds using the catalyst. Optically active hydroxymethylated compounds are obtained with excellent asymmetric selectivity by using a catalyst obtained by mixing chiral ligands (for example, chemical formula 4) with scandium triflate and the like.

Abstract: A silicon enolate represented by the following formula (Formula 1) (in the formula, R5 to R7 represent hydrogen atoms, aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, monocyclic or polycyclic aromatic or aromatic-aliphatic hydrocarbon groups or heterocyclic groups, R5 and R7 are different, R6 is not a hydrogen atom, each R8 may be identical or different and represents a methyl group, ethyl group or isopropyl group) and formaldehyde are allowed to react in an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand comprising a chiral bipyridine compound or its antipode and Bi(OTf)3.

Abstract: The present invention presents a catalyst that allows asymmetric hydroxymethylation reactions to progress with excellent asymmetric selectivity and a production method for optically active hydroxymethylated compounds using the catalyst. Optically active hydroxymethylated compounds are obtained with excellent asymmetric selectivity by using a catalyst obtained by mixing chiral ligands (for example, chemical formula 4) with scandium triflate and the like.

Abstract: A silicon enolate represented by the following formula (Formula 1) (in the formula, R5 to R7 represent hydrogen atoms, aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, monocyclic or polycyclic aromatic or aromatic-aliphatic hydrocarbon groups or heterocyclic groups, R5 and R7 are different, R6 is not a hydrogen atom, each R8 may be identical or different and represents a methyl group, ethyl group or isopropyl group) and formaldehyde are allowed to react in an aqueous solution or a mixed solvent of water and an organic solvent in the presence of a catalyst obtained by mixing a ligand comprising a chiral bipyridine compound or its antipode and Bi(OTf)3.

Abstract: A method for aldol reaction in water, which comprises: reacting an aldehyde with a silyl enol ether in an aqueous medium in the presence of a boronic acid represented by the following general formula (1): R1R2BOH??(1) (wherein R1 and R2 are the same or different hydrocarbon groups that may contain a substituent), a surfactant, and a Brønsted acid is provided. This method for aldol reaction in water uses a catalytic amount of the boron source to give products in high yield and selectivity.

Abstract: An aldol reaction in an aqueous solution between an aldehyde represented by the following formula (I): R—CHO??(I) (wherein R is a hydrocarbon group which may have an substituent), and a silicon enolate represented by the following formula (II): (wherein R1 and R2 are a hydrogen atom or an aliphatic hydrocarbon group, at least one of them being an aliphatic hydrocarbon group; and R3 is a substituent selected from the group consisting of an aliphatic hydrocarbon group, an aromatic hydrocarbon group and a sulfur-containing substituent, wherein R2 and R3 may be combined with each other to form a ring) is performed so as to generate diastereoselectivity by using FeCl3, which is a low-cost Lewis acid, and a surfactant.

Abstract: A method for aldol reaction in water, which comprises: reacting an aldehyde with a silyl enol ether in an aqueous medium in the presence of a boronic acid represented by the following general formula (1):