Abstract: trans-RuH(&eegr;1-BH4)[(S)-xylbinap][(S,S)-dpen] (0.00125 mmol), acetophenone (5.0 mmol), and 2-propanol (2.5 mL) were placed in an autoclave, and the resulting solution was repeatedly subject 5 times to a procedure of performing pressure reduction and argon introduction while stirring the solution for deaeration. A hydrogen tank was then connected to the autoclave, and after replacing the air inside an introduction tube with hydrogen, the pressure inside the autoclave was adjusted to 5 atmospheres and then hydrogen was released until the pressure dropped to 1 atmosphere. After repeating this procedure 10 times, the hydrogen pressure was adjusted to 8 atmospheres and stirring at 25° C. was performed for 12 hours. By concentrating the solution obtained by depressurization and subjecting the crude product to simple distillation, (R)-1-phenylethanol (yield: 95%) in the form of a colorless oily substance was obtained at an ee of 99%.

Abstract: A process for preparing optically active secondary alcohols of the general formula (3), [wherein R1 is linear lower alkyl, an aromatic ring group, or the like; A is CH2NR2R3 or the like; n is an integer of 0 to 2; and * represents an asymmetric carbon atom] by asymmetrically hydrogenating a ketone compound of the general formula (1) having nitrogenous or oxygen functional group at any of the a-, &bgr;- and &ggr;-positions, with selectivity among functional groups by the use of a ruthenium/optically active bidentate phosphine/diamine complex as the catalyst in the presence of hydrogen alone or together with a base. The optically active secondary alcohols obtained by the process are useful as drugs and intermediates for the preparation of drugs.

Abstract: Alcohols are produced in a practical and advantageous method, by the hydrogenation of a carbonyl compound under mild conditions, by reacting the carbonyl compounds with hydrogen in the presence of a bipyridyl derivative, a group VIII transition metal complex, and a base, or by reducing a carbonyl compound in the presence of a bipyridyl derivative, a group VIII transition metal complex, a base, and an alcoholic solvent.

Abstract: The object of the invention is to provide a solvent distillation apparatus capable of preparing a highly pure anoxic, dehydrated solvent. A distilling flask is connected to a vacuum double-barrel fractionating column by a glass flange. The upper end of the fractionating column is connected to a middle portion of a reflux condenser. The upper end of the reflux condenser is provided with an outlet for a purge gas, and the lower end thereof is connected to a condensate reservoir. The base of the condensate reservoir is connected to the fractionating column near a lower end thereof via a Young cock, and also connected to a collecting flask via a Young cock and a glass flange. An immersion tube is used to blow an inactive gas into a base portion of the condensate reservoir. The fractionating column, the reflux condenser and the condensate reservoir are integrated as one body.

Abstract: The object of the invention is to provide a solvent distillation apparatus capable of preparing a highly pure anoxic, dehydrated solvent. A distilling flask is connected to a vacuum double-barrel fractionating column by a glass flange. The upper end of the fractionating column is connected to a middle portion of a reflux condenser. The upper end of the reflux condenser is provided with an outlet for a purge gas, and the lower end thereof is connected to a condensate reservoir. The base of the condensate reservoir is connected to the fractionating column near a lower end thereof via a Young cock, and also connected to a collecting flask via a Young cock and a glass flange. An immersion tube is used to blow an inactive gas into a base portion of the condensate reservoir. The fractionating column, the reflux condenser and the condensate reservoir are integrated as one body.

Abstract: Disclosed is a method of producing an optically active &bgr;-hydroxy sulfonic acid compound comprising hydrogenating a &bgr;-keto sulfonic acid compound represented by formula 1: where R1 represents an alkyl or a phenyl group, which may be substituted, and R2 represents sodium or an alkyl group, in an acidic solvent, in the presence of an asymmetric catalyst comprising a complex of bivalent Ru, having 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand, to produce a compound represented by formula 2: where R1 and R2 are as defined above, and * designates an asymmetric carbon atom.

Abstract: The invention provides a metal complex comprising a ligand and a metal. The ligand is an aminophosphine compound represented by the following formula (1) The metal is rhodium, ruthenium, iridium or nickel.

Abstract: This document describes a novel and practically excellent process for the preparation of optically active compounds, such as optically active alcohols or amines which are useful for various applications, for example, as synthetic intermediates of pharmaceuticals, liquid crystal materials, and reagents for optical resolution, wherein a hydrogen transfer type asymmetric reduction is carried out in the presence of both a transition metal complex and an optically active nitrogen compound or a transition metal complex having an optically active nitrogen compounds as an asymmetric ligand, and a hydrogen-donating organic or inorganic compound.

Abstract: The present invention provides a catalyst for transesterification comprising an organotin compound expressed by the following general formula (I): ##STR1## wherein, X, Y, and Z represent, respectively and independently, an alkoxyl group, alkylthio group, halogen atom, or alkyl group; where at least two groups among X, Y, and Z represent an alkoxyl group, alkylthio group, or halogen atom; R represents an organic chain; and R' represents a hydrogen atom, or alkyl group.

Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.

Abstract: A process whereby 4-t-butylcyclohexanol with a high content of the cis-isomer, which is useful as a perfume ingredient, can be economically produced on an industrially available scale at a low cost. The process comprises hydrogenating 4-t-butylcyclohexanone by using a specific ruthenium-phosphine complex as a catalyst in the presence of a base containing an alkali metal and an alkylenediamine having from 1 to 6 carbon atoms.

Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.

Abstract: The present invention provides a method for producing a alcohol including an optically active alcohol by hydrogenating a carbonyl compound in the presence of a homogeneous catalyst, a base and a nitrogen-containing organic compound. Thus, the reaction employs an inexpensive catalyst and proceeds in high yield and high efficiency.

Abstract: A process whereby trans-3-isocamphylcyclohexanol, which is useful as a perfume ingredient, can be produced on an industrially available scale, at a low cost and at a high stereoselectivity, is disclosed. The process comprises hydrogenating 3-isocamphylcyclohexanone represented by the following formula (I): ##STR1## by using a ruthenium/phosphine complex as a catalyst in the presence of a base containing an alkali metal or an alkaline earth metal and an amine.

Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.

Abstract: Disclosed herein is a process for producing an optically active hydroxyalkylphosphonate represented by the formula (4), which comprises asymmetrically hydrogenating an oxoalkylphosphonate represented by the formula (1) using, as a catalyst, a ruthenium-optically active phosphine complex represented by the formula (2).

Abstract: A process for producing an optically active .gamma.-butyrolactone derivative represented by formula (II): ##STR1## wherein R.sup.1 represents an alkyl group having from 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, is disclosed, comprising enantioselectively hydrogenating a .gamma.-keto acid or an ester thereof represented by formula (I): ##STR2## wherein R.sup.1 and * are as defined above; and R.sup.2 represents a hydrogen atom or a lower alkyl group, in the presence of an optically active ruthenium-phosphine complex. The compounds (I) can be obtained at high optical purity through simple operations and a reduced number of steps.

Abstract: A process for producing a 2,3-disubstituted-4-substituted cyclopentanone, an enantiomorph thereof, or a mixture of these in an arbitrary ratio.The process comprises (A) subjecting a 4-substituted-2-cyclopentenone, an enantiomorph thereof, or a mixture of these in an arbitrary ratio, and an organocopper compound to conjugate addition-reaction, and thereafter (B) reacting the resulting enolate intermediate with a halide in the presence of a phenyl organotin compound.

Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R.sup.2 -BINAP represents a teritary phosphine compound represented by formula (II): ##STR2## wherein R.sup.2 represents a hydrogen atom, a methyl group, a methoxy group, or a t-butyl group; X represents a halogen atom; and R and R.sup.1, which may be the same or different, each represent a phenyl group or a substituted phenyl group, and a ruthenium-phosphine complex represented by formula (III): ##STR3## wherein R and R.sup.1 are as defined above; and dma represents N,N-dimethylacetamide, which is an intermediate for synthesizing the ruthenium-phosphine complex of formula (I), are disclosed. The complex of formula (I) is useful as a catalyst for general syntheses with its ligand being an optically inactive compound or for asymmetric syntheses with its ligand being an optically active compound and, also, can be prepared at a low cost.

Abstract: An isocarbacyclin derivative represented by the following formula [VII'] ##STR1## wherein A represents, a hydrocarbylcarboxylate group, a carboxymethoxycarbonyl group, an amide group, an acyloxymethyl group or a hydroxymethyl group; R.sup.4 represents H, a methyl group or a vinyl group; R.sup.5 represents a (substituted)alkyl group, a phenyl group, a phenoxy group or a cycloalkyl group; R.sup.e22 and R.sup.e32 represent H or a hydroxyprotecting group; n is 0 or 1;and a pharmaceutically acceptable salt thereof.