Takasago International Corporation

Takasago Perfumery Co., Ltd.

Noboru Sayo

Hidenori Kumobayashi

Hidemasa Takaya

Susumu Akutagawa

Takao Saito

Ryoji Noyori

Tohru Yokozawa

Noboru Sano

Takeshi Nakai

Koichi Mikami

Kazuhiko Matsumura

Tetsuro Yamasaki

Takanao Taketomi

Kyoko Tamao

Takero Ishizaki

Masahiro Terada

Kazushi Mashima

Tetsuo Ohta

Xiaoyong Zhang

Dai Kitamoto

Akira Amano

Toshiyuki Murayama

Daisuke Igarashi

Masato Kitamura

Nobuo Yamada

Toshiyuki Takezawa

Yasushi Kato

Hideki Nara

Masaki Shimizu

Takeshi Ohkuma

Takahiro Fujiwara

Misao Yagi

Takaji Matsumoto

Yoshiki Okeda

Yoshifumi Yuasa

Nobuo Seido

Tsukasa Sotoguchi

Tetsuo Tomita

Sotaro Miyano

Akifumi Yoshida

Martin F Giles

Takashi Ohshima

Tetsutaro Hattori

Tatsuya Ohmoto

Tetsuo Ota

Satoru Matsukawa

Koji Inagaki

Xiaoyaong Zhang

Takanori Iwasaki

Osamu Uesugi

Yasufumi Tamai

Shinichi Inoue

Toshiro Takemasa

Susumo Akutagawa

Hiroyuki Nagashima

Hidonori Kumobayashi

Toshinobu Korenaga

Satoshi Mano

Nozomu Sakai

Tatsuya Omoto

Ryoli Noyori

Disclosed is a selective ester production process of an alcoholic hydroxyl group, which proceeds under chemically mild conditions, while having adequate environmental suitability, operability and economical efficiency. Specifically disclosed is a process for producing an ester compound, which is characterized in that an alcohol and a carboxylic acid ester compound are reacted in the presence of a compound containing zinc element, thereby selectively acylating a hydroxyl group of the alcohol.

Acylation reaction of hydroxyl group

Provided is a method for producing a ruthenium complex comprises the step of reacting a ruthenium compound represented by general formula (1):[RuX(L)(PP)]X&#x2003;&#x2003;(1),wherein Ru represents a ruthenium atom; X represents a halogen atom; L represents an arene; and PP represents an optically active bisphosphine,with a carboxylate salt represented by general formula (2):RCOM&#x2003;&#x2003;(2),wherein M represents a monovalent cation; and Rrepresents a group selected from the group consisting of alkyl groups, haloalkyl groups, phenyl groups optionally having a substituent(s), 1-aminoalkyl groups and 1-amino-1-phenylalkyl groups,

Method for producing a ruthenium complex

The present invention provides a water-soluble transition metal-diamine complex which can be easily separated from reaction products through liquid separation, etc. and is recycleable; an optically active diamine compound constituting the ligand of the complex; and a catalyst for asymmetric synthesis which comprises these. The present invention relates to a water-soluble optically active transition metal-diamine complex represented by the formula (2): [wherein Rand Reach represents hydrogen, a hydrocarbon group, &#x2014;SOR(wherein Ris a hydrocarbon group, substituted amino, etc.), etc.; Rto Reach represents hydrogen, a hydrocarbon group, alkoxy, substituted amino, etc.; M represents a transition metal; X represents halogen; L represents a ligand; and * indicates an asymmetric carbon atom; provided that at least one of Rto Rand Rto Ris substituted amino], a catalyst for asymmetric synthesis containing the complex, and a process for producing an optically active alcohol, which comprises using the catalyst to asymmetrically reduce a ketone.

Optically active transition metal-diamine compound and process for producing optically active alcohol with the same

[PROBLEMS] To provide a method by which desired optically active carboxylic acids may be prepared from a carboxylic acid having a carbon-carbon double bond through asymmetric hydrogenation with a catalyst consisting of a transition metal complex containing a water-soluble ligand and which permits easy separation of the used catalyst from the product by liquid-liquid separation alone and enables the recovery of an expensive transition metal and the reuse of the catalyst. [MEANS FOR SOLVING PROBLEMS] Phosphines represented by the general formula (1):  wherein Xis oxygen or methylene; Xis methylene, ethylene, trimethylene, 1,2-dimethylethylene, isopropylidene, or difluoromethylene; A is a Group IA alkali metal of the periodic table, hydrogen, or an ammonium ion; and a, b, c and d are each an integer of 0 or 1, with the proviso that the cases wherein the sum of a, b, c, and d is 0 are excepted.

Phosphines, transition metal complexes containing the same as the ligand, and process for production of optically active carboxylic acids

Process for producing an optically active ruthenium-phosphine complex and process for producing an optically active alcohol by using the complex

A novel process in which an optically active alcohol compound having a desired absolute configuration and a high optical purity can be obtained by asymmetrically hydrogenating a &bgr;-keto acid compound through a simple operation. An optically active alcohol represented by general formula (III) as defined is obtained by asymmetrically hydrogenating a &bgr;-keto ester compound represented by general formula (I) as defined in the presence of at least one ruthenium complex having as a ligand an optically active tertiary diphosphine compound represented by general formula (II) as defined.

Process for producing optically active alcohol

A process for producing a diphosphine oxide or diphosphonate represented by formula (1) as defined, which comprises treating, with a base, a phosphine compound represented by formula (2) as defined and adding the thus-treated phosphine compound to a nonpolar solvent having an oxidative metal compound suspended therein so as to effect dimerization. The present invention makes it possible to produce, conveniently, in a high yield and safely, a diphosphine oxide or diphosphonate which is an intermediate for producing a diphosphine compound useful as a ligand of a metal complex serving as a catalyst for asymmetric synthesis reaction.

Production process of diphosphine oxide and diphosphonate

Phosphine derivative and polymer thereof and transition metal complex comprising the same

Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.

Method for producing 1-menthol

This invention provides a novel diphosphine compound which is useful as a ligand of catalysts for asymmetric synthesis reactions, particularly asymmetric hydrogenation reaction. Particularly, it provides a diphosphine compound represented by a general formula (1):

Optically active diphosphine compound, production intermediate thereof, transition metal complex containing the compound as ligand and asymmetric hydrogenation catalyst containing the complex

Ruthenium-phosphine complex and method for producing the same

Disclosed is a process for producing an optically active .beta.-lactone represented by the general formula (I): ##STR1## wherein R.sup.1 represents an alkyl group having 1-9 carbon atoms which can be branched or a cycloalkyl group having 5-7 carbon atoms. The process comprises reacting an aldehyde represented by the general formula (II):

Process for producing optically active .beta.-lactones

The present invention provides a method for making compound (1) by reacting compound (2) with phosphine oxide (3) in the presence of a transition metal/phosphine complex and optionally reducing the reaction product: ##STR1## where n represents 0 or 1; the double line having a continuous line and a dotted line represents a double bond or a single bond such that the ring having the double line forms a naphthalene ring or an octahydronaphthalene ring with an adjacent benzene ring; Tf represents a trifluoromethanesulfonyl group; and Ar represents a phenyl group, a substituted phenyl group or a naphthyl group. The present invention provides an economical way to produce compound (1) as a ligand of a complex useful as a catalyst for a variety of asymmetric synthesis reactions.

Method for making an optically active diphosphine ligand

Disclosed is a ruthenium-phosphine complex represented by formula (I):

Process for preparing ruthenium-phosphine complex

The present invention provides a ligand for a novel catalyst superior in such characteristics as selectivity (chemoselectivity and enantioselectivity) and catalytic activity in asymmetric synthesis reactions and a ligand for a novel catalyst effective in an asymmetric hydrogenation reaction in particular. The ligand is an optically active diphosphine compound represented by the following formula: ##STR1## where Ph is a phenyl group, X is a chlorine or bromine atom, and R.sup.1 and R.sup.2 are each an alkyl group having 1 to 3 carbon atoms.

Optically active diphosphine compound, method for making the compound,

Growing community of inventors

Kanagawa, Japan

Noboru Sayo