Takasago International Corporation

Tokyo University of Agriculture and Technology

Meiji Seika Pharma Co., Ltd.

National University Corporation Tokyo University of Agriculture and Technology

Tohru Yokozawa

Noboru Sayo

Takao Saito

Hideki Nara

Kazuhiko Matsumura

Hidenori Kumobayashi

Kenji Yagi

Toshiyuki Murayama

Wataru Kuriyama

Tsukasa Sotoguchi

Takero Ishizaki

Xiaoyong Zhang

Motonobu Takenaka

Takashi Moroi

Ken Tanaka

Masaaki Mitomi

Nobuto Minowa

Tetsuro Yamasaki

Nozomu Nakanishi

Takahiro Fujiwara

Tomohiko Hakamata

Akifumi Yoshida

Tatsuya Ohmoto

Noburo Sayo

Xiaoyaong Zhang

Tatsuya Omoto

The present invention provides a novel ruthenium complex which has an excellent catalytic activity in terms of reactivity for asymmetric reduction of a carbonyl compound and enantioselectivity, a catalyst using the ruthenium complex, and a method for preparing optically active alcohol compounds using the ruthenium complex. The present invention relates to a ruthenium complex having ruthenacycle structure, a catalyst for asymmetric reduction consisting of the ruthenium complex, and a method for preparing optically active alcohol using the ruthenium complex.

Ruthenium complex and method for preparing optically active alcohol compound

An optically active compound represented by the following formula (5): wherein, in the formula (5), Rand Rmay be the same or different are an alkyl group optionally having a substituent group selected from the group consisting of an alkoxy group and a halogen atom, a cycloalkyl group optionally having a substituent group selected from the group consisting of an alkoxy group and a halogen atom, an aryl group optionally having a substituent group selected from the group consisting of an alkyl group, an alkoxy group and a halogen atom, an alkoxy group optionally having a substituent group selected from the group consisting of a halogen atom and an aryl group or an aryloxy group optionally having a substituent group selected from the group consisting of an alkyl group, an alkoxy group and a halogen atom; a1 and a2 independently are 0 or 1; and * is axial asymmetry.

Axially asymmetric phosphorus compound and production method thereof

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

The present invention is a process for producing optically active aminophosphinylbutanoic acids represented by the formula (2), comprising asymmetrically hydrogenating a compound represented by the formula (1) in the presence of a ruthenium-optically active phosphine complex, a process for the production thereof, and a compound useful in a herbicide such as L-AHPB that can be produced with good efficiency and high asymmetric yield.

Process for production of optically active aminophosphinylbutanoic acids

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

Provided is a method for producing an optically active compound, in more detail, for producing an optically active compound by asymmetric hydrogenation in a high yield and asymmetric yield. The present invention also provides a catalyst for asymmetric synthesis for the above production method, especially a catalyst for asymmetric hydrogenation, containing a transition metal complex. Further, the present invention provides a new diphosphine compound useful as a ligand of the above transition metal complex and a new transition metal complex containing the above diphosphine compound. The present invention relates to a diphosphine compound represented by the following formula (1): a transition metal complex using the compound, a catalyst for asymmetric synthesis comprising the above transition metal complex and a method for producing an optically active compound using the above catalyst for asymmetric synthesis.

Substituted optically active disphosphine compound

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

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

A novel diphosphine compound of the formula (I): ##STR1## where R.sup.1 and R.sup.2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.

Chiral diphosphine compound intermediate for preparing the same

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,

A novel chiral unsymmetric diphosphine compound of formula (I): ##STR1## wherein Ar.sup.1 and Ar.sup.2, which are different from each other, each represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a furfuryl group, a benzofurfuryl group, a thienyl group, or a benzothienyl group, and a transition metal complex containing the diphosphine compound as a ligand. The complex catalyzes various asymmetric synthesis reactions, e.g., asymmetric hydrogenation or asymmetric hydrosilylation, exhibiting excellent performance in selectivity, conversion and catalytic activity, to provide a product of desired absolute configuration at high optical purity and in high yield.

Chiral unsymmetric diphosphine compound and transition metal complex

The present invention provides a method for producing novel optically active diphosphine compounds �2,2'-bis(di-substituted phosphino)-1,1'-binaphthyl compounds! having a selectivity (chemoselectivity or enantioselectivity) and catalytic activity different from those of conventional BINAP compounds. In a method of the present invention for producing an optically active diphosphine compound (i.e., 2,2-bis(di-substituted phosphino)-1,1'-binaphthyl), 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl is reacted, in the presence of a transition metal-phosphine complex, with a phosphineoxide compound represented by the following general formula:

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Kanagawa, Japan

Tohru Yokozawa