Takasago International Corporation

Kanto Kagaku Kabushiki Kaisha

Nagoya Industrial Science Research Institute

Nippon Soda Co., Ltd.

Hokkaido University

Other

Mitsubishi Rayon Company, Limited

Research Development Corporation of Japan

Takeshi Ohkuma

Ryoji Noyori

Noriyoshi Arai

Kunihiko Murata

Takao Ikariya

Hidenori Kumobayashi

Tsutomu Inoue

Kazuhiko Matsumura

Masato Kitamura

Nobuo Seido

Hirohito Oooka

Takeaki Katayama

Kunihiko Tsutsumi

Masaya Akashi

Nobuhito Kurono

Noboru Sayo

Masahito Watanabe

Shohei Hashiguchi

Masami Kozawa

Hideyuki Ikehira

Junichi Hori

Makoto Emura

Noriyuki Utsumi

Christian A Sandoval

Takaaki Toyoda

Masatoshi Koizumi

Kilian Mu&ntilde;iz

Toru Yokozawa

Eiji Katayama

Hirohito Ooka

A method for producing, in a few simple steps, a specific optically active aldehyde represented by the general formula (1), in which * is an asymmetric carbon atom, includes asymmetrically isomerizing a specific allyl alcohol represented by the general formula (2) in the presence of a ruthenium complex and a base.

Method of producing optically-active aldehyde

A process for producing an optically active amine compound, characterized by asymmetrically hydrogenating a prochiral carbon-nitrogen double bond in the presence of a ruthenium complex represented by general formula (1) or (2) (wherein Prepresents an optically active diphosphine, X represents an anionic group, and Ar represents an optionally substituted arylene group). 

Process for producing optically active amine

Methods are provided for producing an optically active secondary alcohol at a high optical purity by hydrogenating a substrate carbonyl compound at a high efficiency using as a catalyst a ruthenium complex bearing as a ligand certain optically active diphosphine compound and a readily synthesized amine compound. For example, aromatic ketones and heteroaromatic ketones are reacted with hydrogen and/or a hydrogen donating compound in the presence of the ruthenium complex.

Process for producing optically active secondary alcohol

A process is provided for efficiently producing an optically active 3-quinuclidinol derivative of high optical purity using a readily available ruthenium compound as an asymmetric reduction catalyst. This process is a process for producing an optically active 3-quinuclidinol derivative represented by the following formula (III) comprising asymmetrically hydrogenating a 3-quinuclidinone derivative represented by the following formula (I) in the presence of a ruthenium compound (II) represented by formula (II): Ru(X)(Y)(Px)[RRC*(NRR)-A-RRC*(NRR)] (in the formulas, R represents a hydrogen atom or C7 to C18 aralkyl group and the like, X and Y represent hydrogen atoms or halogen atoms and the like, Px represents a phosphine ligand, n represents 1 or 2, R1 to R8 represent hydrogen atoms or C1 to C20 alkyl groups and the like, * represents an optically active carbon atom and A represents an ethylene group and the like). 

Production process of optically active 3-quinuclidinol derivative

The present invention can provide a cyanation catalyst represented by the general formula (I): 

Cyanation catalyst and method for producing optically active cyanhydrin compound using the same

A hydrogenation promoter of the present invention is produced by reacting an alkyne compound or an alkene compound, a palladium compound represented by a general formula Pd(II)XL(where L represents a monodentate ligand or a polydendate ligand other than a phosphorus-containing ligand (when two or more Ls are present in the compound, the Ls may be the same or different), X represents an anionic group, j represents a value determined according to the valence of X so that Xhas a valence of &#x2212;2 as a whole, and k represents an integer in the range of 0 to 4), and a base in an organic solvent. Specifically, The hydrogenation promoter of the invention includes palladium nanoparticles containing the alkyne compound or the alkene compound as an agglomeration-preventing agent.

Hydrogenation promoter, hydrogenation catalyst, and process for producing alkene compound

A sulfonate catalyst represented by the formula below and a ketone compound are placed in a solvent, and the ketone compound is hydrogenated by mixing in the presence of hydrogen to produce an optically active alcohol. 

Sulfonate catalyst and method of producing alcohol compound using the same

A tert-alkyl ketone, pinacolone was hydrogenated under pressurized hydrogen in the presence of a ruthenium complex (S)-1 and a base, and corresponding (S)-3,3,-dimethyl-2-butanol was thereby obtained in 100% yield and 97% ee 

Ruthenium complex and process for producing tert-alkyl alcohol therewith

trans-RuH(&eegr; -BH )&lsqb;(S)-xylbinap&rsqb;&lsqb;(S,S)-dpen&rsqb; (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&deg; 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%.

Synthesis of ruthenium-hydride complexes and preparation procedures of chiral alcohols and ketones

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.

Processes for the preparation of alcohols

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.

Process for producing cis-4-t-butylcyclohexanol

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.

Method for producing an alcohol

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.

Process for producing optically active .gamma.-butyrolactone derivatives

A process for preparing carnitine which comprises asymmetrically hydrogenating a .gamma.-halogeno-.beta.-keto ester represented by formula (I): ##STR1## wherein X represents a chlorine atom or a bromine atom; and R represents a lower alkyl group, in the presence of a ruthenium-optically active phosphine complex represented by formula (II), (III) or (IV):

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Sapporo, Japan

Takeshi Ohkuma