Patents by Inventor Noboru Sayo
Noboru Sayo has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5324870Abstract: A process for producing an optically active 1-substituted-1,3-propanediol is disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of a ruthenium-phosphine complex represented by formula (I):[RuI(p-cymene)(R.sup.1 BINAP)]I.sub.3 (I)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by formula (II): ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position.Type: GrantFiled: November 23, 1993Date of Patent: June 28, 1994Assignee: Takasago International CorporationInventors: Noboru Sano, Noboru Sayo, Hidenori Kumobayashi
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Patent number: 5286888Abstract: A ruthenium-phosphine complex is disclosed, represented by formula (I):[RuI(p-cymene)(R.sup.1 -BINAP)]I.sub.3 (I)where R.sup.1 -BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position. A process for producing an optically active 1-substituted-1,3-propanediol is also disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of the ruthenium-phosphine complex of formula (I).Type: GrantFiled: October 22, 1992Date of Patent: February 15, 1994Assignee: Takasago International CorporationInventors: Noboru Sano, Noboru Sayo, Hidenori Kumobayashi
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Patent number: 5206399Abstract: 2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl represented by formula (I). ##STR1## is disclosed. A transition metal complex containing the same, a process for producing 2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl, and a process for producing 2,2'-bis(diphenylphosphinyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl are also disclosed.Type: GrantFiled: October 1, 1991Date of Patent: April 27, 1993Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi
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Patent number: 5198562Abstract: 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.Type: GrantFiled: August 1, 1991Date of Patent: March 30, 1993Assignee: Takasago International CorporationInventors: Ryoji Noyori, Masato Kitamura, Noboru Sayo, Hidenori Kumobayashi, Martin F. Giles
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Patent number: 5155240Abstract: A process for producing an optically active dihydropyran derivative represented by formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each represents a hydrogen atom, a lower alkyl group, a tri-lower alkylsilylmethyl group, a lower alkoxycarbonylamino group, or an --OR.sup.5 group, wherein R.sup.5 represents a lower alkyl group, a lower acyl group, a lower alkoxycarbonyl group, a di-lower alkylcarbamoyl group, or a tri-lower alkylsilyl group, or R.sup.1 and R.sup.2 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, or R.sup.2 and R.sup.3 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, provided that all of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 do not represent hydrogen atoms at the same time; and R.sup.6 represents a lower alkyl group, which comprises reacting a diene compound represented by formula (2): ##STR2## wherein R.Type: GrantFiled: March 13, 1991Date of Patent: October 13, 1992Assignee: Takasago International CorporationInventors: Koichi Mikami, Masahiro Terada, Takeshi Nakai, Noboru Sayo
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Patent number: 5066815Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: May 8, 1990Date of Patent: November 19, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4994590Abstract: A ruthenium-phosphine complex represented by formula (I)[RuX.sub.l (L).sub.m (R-BINAP)]Y.sub.n (I)wherein R-BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R represents a hydrogen atom or a methyl group; X represents a halogen atom; L represents substituted or unsubstituted benzene or acetonitrile; Y represents a halogen atom, CLO.sub.4, PF.sub.6, BPh.sub.4 (wherein Ph represents a phenyl group) or BF.sub.4 ; when L is substituted or unsubstituted benzene, l represents 1, m represents 1, and n represents 1; and whe L is acetonitrile, when l is 1, then m represents 2, and n represents 1, and when l is 0, the m represents 4, and n represent 2. The complex exhibits excellent catalytic activity in asymmetric reactions to provide a product of high optical purity. The complex can be produced at low cost.Type: GrantFiled: October 24, 1989Date of Patent: February 19, 1991Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Kazushi Mashima, Hidenori Kumobayashi, Noboru Sayo
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Patent number: 4994602Abstract: A process for preparing an optically active 6-t-butoxy-3,5-dihydroxyhexanoic ester represented by formula: ##STR1## wherein t-Bu represents a t-butyl group; and R.sup.4 represents a lower alkyl group, which is useful as a precursor of a lactone moiety of campactin, mevinolin or analogues thereof is disclosed, comprising asymmetrically hydrogenating a 4-t-butoxyacetoacetic ester in the presence of a ruthenium-optically active phosphine complex to obtain an optically active 4-t-butyoxy-3-hydroxybutanoic ester, reacting the ester with a lithium enolate of an acetic ester to obtain an optically active 6-t-butyoxy-5-hydroxy-3-oxohexanoic ester, and asymmetrically hydrogenating the resulting ester in the presence of a ruthenium-optically active phosphine complex as a catalyst. The desired product can be obtained in good yield at high stereoselectivity.Type: GrantFiled: February 27, 1990Date of Patent: February 19, 1991Assignee: Takasago International CorporationInventors: Nobuo Seido, Noboru Sayo, Hidenori Kumobayashi
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Patent number: 4981992Abstract: A process for preparing an optically active 3-hydroxybutanoic acid represented by formula (I): ##STR1## wherein: R.sup.1 represents a protective group of carboxylic acid, andR.sup.2 represents a hydrogen atom; a lower alkyl group which may be substituted with a halogen atom; a lower alkoxy group; a phenyl group which may be substituted with a lower alkyl group or a lower alkoxy group; or a benzyloxy group which may be substituted with a lower alkyl group or a lower alkoxy group,is disclosed, comprising asymmetrically hydrogenating a 3-oxobutanoic acid ester represented by formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. The compound of formula (I) which is useful for synthesizing a 4-acetoxyazetidin-2-one derivative, a useful intermediate for obtaining penem antibiotics, can be prepared economically.Type: GrantFiled: November 14, 1989Date of Patent: January 1, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Yoshiki Okeda, Hiroyuki Nagashima, Hidonori Kumobayashi
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Patent number: 4965398Abstract: A process for preparing an .alpha.-hydroxycarboxylate represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 and R.sup.2 are bonded to each other to form a five- to seven-membered cycloalkenyl or bicycloalkenyl ring which may be substituted with a lower alkyl group; and R.sup.3 represents a lower alkyl group,which comprises reacting an olefin compound represented by formula (II): ##STR2## wherein R.sup.1 ' represents a hydrogen atom or a lower alkyl group; and R.sup.2 ' represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 ' and R.sup.2 ' are bonded to each other to form a five- to seven-membered cycloalkyl or bicycloalkyl ring which may be substituted with a lower alkyl group,with a glyoxylate represented by formula (III): ##STR3## wherein R.sup.Type: GrantFiled: July 28, 1989Date of Patent: October 23, 1990Assignee: Takasago International CorporationInventors: Koichi Mikami, Masahiro Terada, Takeshi Nakai, Noboru Sayo, Hidenori Kumobayashi
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Patent number: 4962230Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.Type: GrantFiled: November 16, 1987Date of Patent: October 9, 1990Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4962242Abstract: A process for producing an optically active alcohol represented by formula (I): ##STR1## wherein R.sub.1 is an alkyl group having from 2 to 11 carbon atoms, an alkenyl group having from 3 to 11 carbon atoms, an alkadienyl group having from 6 to 11 carbon atoms, a cyclohexyl group, an cyclohexylmethyl group, or a cyclohexylethyl group, provided that the olefin in the alkenyl group or alkadienyl group is not conjugated to the olefin at the 2-position thereof; and * means an asymmetric carbon atom,is disclosed, comprising subjecting an olefinic alcohol represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above to asymmetric hydrogenation in the presence of, as a catalyst, a ruthenium-optically active phosphine complex.According to the process of the invention, the desired optically active alcohols which are useful not only as intermediates for the manufacture of perfumes and vitamin E but also as liquid crystal materials can be produced with high optical purities.Type: GrantFiled: June 25, 1987Date of Patent: October 9, 1990Assignee: Takasago Perfumery Co., Ltd.Inventors: Nobuo Yamada, Toshiyuki Takezawa, Noboru Sayo, Misao Yagi, Hidenori Kumobayashi, Susumu Akutagawa, Hidemasa Takaya, Shinichi Inoue, Ryoji Noyori
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Patent number: 4954644Abstract: A ruthenium-phosphine complex is disclosed, which is represented by formula (I):[Ru(R-BINAP)MCl.sub.k ].sub.l X.sub.m (I)wherein R-BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R represents hydrogen atom or methyl group; M represents Zn, Al, Ti, or Sn; X represents N(C.sub.2 H.sub.5).sub.3 or CH.sub.3 CO.sub.2 ; in the case that X represents N(C.sub.2 H.sub.5).sub.3, l is 2 and m is 1, and when M represents Zn, then k is 4, when M represents Al, then k is 5, and when M represents Ti or Sn, then k is 6; and in the case that X represents CH.sub.3 CO.sub.2, l is 1 and m is 2, and when M represents Zn, then k is 2, when M represents Al, then k is 3, and when M represents Ti or Sn, then k is 4.Type: GrantFiled: September 7, 1988Date of Patent: September 4, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Toshiro Takemasa, Hidenori Kumobayashi
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Patent number: 4933482Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a .beta.-keto acid derivative in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 9, 1988Date of Patent: June 12, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4766225Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a methyl group, or a methoxy group; and R.sup.2 represents a lower alkyl group, a halogenated lower alkyl group, a phenyl group, or a phenyl group substituted with a lower alkyl group. The complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.Type: GrantFiled: December 9, 1987Date of Patent: August 23, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4766227Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R represents a hydrogen atom, a methyl group, or a methoxy group; and X represents ClO.sub.4, BF.sub.4, or PF.sub.6. The ruthenium-phosphine complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.Type: GrantFiled: December 9, 1987Date of Patent: August 23, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4764629Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R represents a hydrogen atom, a methyl group, or a methoxy group; S represents a tertiary amine; when y is 0, then x is 2, z is 4, and p is 1; and when y is 1, then x is 1, z is 1, and p is 0. The complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, and particularly asymmetric hydrogenation.Type: GrantFiled: November 25, 1987Date of Patent: August 16, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4739084Abstract: A ruthenium-phosphine complex having a 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl or its derivative as a ligand and carboxyl groups bonded to the ruthenium atom thereof is disclosed. The complex is inexpensive and exhibits excellent performances as a catalyst for various organic syntheses, and particularly for asymmetric hydrogenation.Type: GrantFiled: April 15, 1987Date of Patent: April 19, 1988Assignee: Takasago Perfumery Co., Ltd.Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Nobuo Yamada, Toshiyuki Takezawa, Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4739085Abstract: A ruthenium-phosphine complex represented by formula (I):[RuH.sub.l (R-BINAP).sub.m ]X.sub.n' (I)wherein R-BINAP is a tertiary phosphine represented by formula (II): ##STR1## R is a hydrogen atom or a methyl group; X is a ClO.sub.4, BF.sub.4, or PF.sub.6 ; and when l is 0, then m is 1 and n' is 2, and when l is 1, then m is 2 and n' is 1, is disclosed. The complex is inexpensive and exhibits excellent performances as a catalyst for various organic syntheses, and particularly for asymmetric hydrogenation.Type: GrantFiled: June 15, 1987Date of Patent: April 19, 1988Assignee: Takasago Perfumery Co., Ltd.Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoli Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa