Takasago International Corporation

Tokyo University of Agriculture and Technology

Wataru Kuriyama

Osamu Ogata

Hideo Shimizu

Daisuke Igarashi

Yukinori Yusa

Yasunori Ino

Hideki Nara

Kazuhiko Matsumura

Kenji Yagi

Toshiyuki Murayama

Tohru Yokozawa

Takaji Matsumoto

Tsukasa Sotoguchi

Motonobu Takenaka

Takashi Moroi

Ken Tanaka

Taichiro Touge

Akifumi Yoshida

Kiyoto Hori

Kunimori Aoki

Disclosed herein is a method for producing an alcohol and an amine from an amide under an atmosphere of hydrogen with the use of, as a catalyst, a ruthenium complex that is easily prepared, easy to handle, and relatively cheaply obtained. Specifically, the method is a method for producing an alcohol and/or an amine from an amide compound under an atmosphere of hydrogen with the use of as a catalyst, a ruthenium carbonyl complex represented by the following general formula (1): RuXY(CO)(L) (1) wherein X and Y may be the same or different from each other and each represents an anionic ligand and L represents a tridentate aminodiphosphine ligand containing two phosphino groups and a &#x2014;NH&#x2014; group.

Method for producing alcohol and/or amine from amide compound

Provided by the present invention is a method for efficient oxidation of alcohols by using, as a catalyst for dehydrogenation oxidation, a ruthenium complex which can be easily produced and easily handled and is obtainable at a relatively low cost. The invention relates to a method of producing a compound having a carbonyl group by dehydrogenation oxidation of alcohols by using as a catalyst the ruthenium carbonyl complex represented by the following general formula (1) RuXY(CO)(L) (1) (in the general formula (1), X and Y may be the same or different from each other and represent an anionic ligand, and L represents a tridentate aminodiphosphine ligand).

Method for producing compound with carbonyl group by using ruthenium carbonyl complex having tridentate ligand as dehydrogenation oxidation catalyst

An object of the present invention is to provide a method for reducing a halogenobenzoic acid ester, in which dehalogenation is inhibited, by using a readily available catalyst. The method comprises reducing an ester with hydrogen gas by using an aromatic hydrocarbon as a solvent in the presence of a ruthenium complex represented by the following general formula (1):RuXY(CO)(L)&#x2003;&#x2003;(1) 

Method for reducing halogenobenzoic acid ester using ruthenium carbonyl complex

Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

Homogeneous asymmetric hydrogenation catalyst

Provided is an alcohol production method comprising the step of reducing an ester or a lactone with hydrogen to produce a corresponding alcohol without addition of a base compound by using, as a catalyst, a ruthenium complex represented by the following general formula (1):RuH(X)(L)(L)&#x2003;&#x2003;(1)wherein

Alcohol production method by reducing ester or lactone with hydrogen

Homogeneous asymmetric hydrogenation process

The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1):RuXY(CO)(L)&#x2003;&#x2003;(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a &#x2014;NH&#x2014; group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.

Ruthenium carbonyl complex having tridentate ligand, its production method and use

Alcohol production method by reducing ester of lactone with hydrogen

Disclosed is an industrially advantageous production method of optically active &#x3b2;-amino acid of formula (5), which includes subjecting an enaminoester of formula (4) to an asymmetric hydrogenation: 

Method for producing an optically active tetrahydroquinoline

A phosphorus compound of formula (1): wherein Rdenotes a hydrogen atom or a hydroxy protective group; Rdenotes a group defined by the following formula (R-1) or (R-2); R, R, R, and Rmay be the same or different and independently denote a hydrogen atom, an alkyl group, an alkoxy group, an acyloxy group, a halogen atom, a haloalkyl group, or a dialkylamino group; two among R, R, R, and Rmay form an aromatic ring optionally having a substituent group, and two among R, R, R, and Rmay form a methylene chain optionally having a substituent group or a (poly)methylenedioxy group optionally having a substituent group: wherein (R-1) and (R-2), Rdenotes an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, or an aryloxy group; Rand Rindependently denote a hydrogen atom, an alkyl group, or an aryl group; z denotes a divalent group; and a denotes an integer of 0 or 1.

Optically active biaryl phosphorus compound and production process thereof

The present invention provides an industrially advantageous production method of optically active tetrahydroquinolines of formula (1), which comprises:      

A method for producing alcohols which comprises reducing esters or lactones with hydrogen gas in the presence of a catalyst comprising (i) a ruthenium compound, (ii) a monodentate monophosphine or a bidentate bisphosphine, and (iii) an amine. Examples of the catalyst include a ruthenium (Ru) complex represented by the formula:RuXX(L)(L)[Xand Xeach represent an anionic ligand, Lrepresents a phosphine ligand, m is 1 when Lis bidentate, while m is 2 when Lis monodentate, Lrepresents an amine ligand, and n is 1 when Lis bidentate, while n is 2 when Lis monodentate.] and a catalyst comprising an amine and a ruthenium (Ru) complex of the formula: RuXX(L)[Lrepresents a monophosphine ligand and r is 3 or 4.].

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Hiratsuka, Japan

Wataru Kuriyama