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2. 发明公开

EP0901997A1 Process for producing optically active alcohol compound 有权
标题翻译：一种用于生产光学活性醇的方法
公开(公告)号：EP0901997A1
公开(公告)日：1999-03-17
申请号：EP98116570.7
申请日：1998-09-02
申请人： Takasago International Corporation , T. Hasegawa Co., Ltd.
发明人： Noyori, Ryoji , Mikami, Koichi , Ohkuma, Takeshi , Terada, Masahiro , Doucet, Henri, c/o Department of Chemistry , Pham Thi Mai Trang, Catherine, c/o Dept. of Chem. , Korenaga, Toshinobu , Ito, Masamichi, c/o T. Hasegawa Co., Ltd. , Sayou, Noboru, c/o Takasago International Corp.
IPC分类号： C07C29/145 , B01J31/24
CPC分类号： C07C29/145 , B01J31/1805 , B01J31/2409 , B01J31/2433 , B01J31/2452 , B01J31/2457 , B01J2231/643 , B01J2531/0266 , B01J2531/821 , C07B2200/07 , C07C2601/16 , C07C2603/24 , C07C33/22 , C07C33/18 , C07C35/18
摘要： Disclosed is a process for producing an optically active alcohol compound represented by formula (II):
wherein R 1 represents an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 represents an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, or R 2 forms, together with R 1 and the adjacent carbon atom, an optionally substituted aliphatic ring, and * represents the location of an asymmetric carbon atom, with high purity and high yield and at low cost by an industrially advantageous method, which comprises subjecting a carbonyl compound represented by formula (I):
wherein R 1 and R 2 are as defined above,
to asymmetric hydrogenation in the presence of a transition metal complex containing a transition metal and a tertiary phosphine as a bidentate ligand, a base and a diamine wherein the diamine is an optically active substance when the tertiary phosphine as a bidentate ligand is a racemic compound, or the diamine is a racemic compound when the tertiary phosphine as a bidentate ligand is an optically active substance.

3. 发明公开

EP0470756A2 Ruthenium-phosphine complex useful as catalyst and intermediate for synthesis thereof 失效
标题翻译： Rathenium膦络合物可用作催化剂及其制造中间体。
公开(公告)号：EP0470756A2
公开(公告)日：1992-02-12
申请号：EP91307028.0
申请日：1991-07-31
申请人： Takasago International Corporation
发明人： Noyori, Ryoji , Kitamura, Masato , Sayo, Noboru , Kumobayashi, Hidenori , Giles, Martin F.
IPC分类号： C07F15/00 , B01J31/24
CPC分类号： B01J31/2404 , B01J31/1805 , B01J31/2452 , B01J2231/643 , B01J2531/821 , C07C67/31 , C07F15/0053 , C07C69/675
摘要： A ruthenium-phosphine complex is represented by formula (I) :
wherein R 2- BINAP represents a tertiary phosphine compound represented by formula (II) :
where R 2 is a hydrogen atom or a methyl, methoxy or a t-butyl, X is a halogen atom ; and R and R 1 each represent is an optionally substituted phenyl group, e. g. substituted with alkyl, alkoxy or dialkylamino. A novel rutheniumphosphine complex used as starting material is represented by formula (III) :
wherein R and R 1 are as above and dma represents N,N-dimethylacetamide and is reacted with BINAP in a solvent to make the complex (I).
The complex of formula (I) is useful as a catalyst for general organic syntheses with its ligand being an optically inactive compound or for asymmetric syntheses with its ligand being an optically active compound, and can be prepared at a low cost.
摘要翻译：钌 - 膦配合物是式（I）表示：其中，R <2> -BINAP darstellt由式表示的叔膦化合物（II）：其中R <2>是一个氢原子或甲基基，甲氧基或叔丁基，X是卤原子; R和R <1>分别表示为任选substituiertem苯基，E。克烷基，烷氧基或二烷基氨基substituiertem。用作起始材料的新型rutheniumphosphine络合物由式（III）表示： worin R和R <1>是N，N-二甲基乙酰胺如上述和DMA darstellt并进行反应与BINAP在溶剂中，使复合物（我）。式（I）的配合物是作为与它的配体是具有光学活性的化合物或与其配体是光学活性的化合物不对称合成一般的有机合成中用作催化剂的，并能以低成本制备。

4. 发明公开

EP0295890A2 Process of preparing optically active alcohol 失效
标题翻译： Herstellungsverfahren eines optisch aktiven Alkohols。
公开(公告)号：EP0295890A2
公开(公告)日：1988-12-21
申请号：EP88305461.1
申请日：1988-06-15
申请人： Takasago International Corporation
发明人： Sayo, Noboru , Kumobayashi, Hidenori , Akutagawa, Susumu , Noyori, Ryoji , Takaya, Hidemasa
IPC分类号： C07C29/136 , C07C31/20 , C07C33/36 , C07C35/06 , C07C35/14 , C07C67/31 , C07C51/367 , C07C41/26 , C07C213/00
CPC分类号： C07C29/145 , C07B2200/07 , C07C41/26 , C07C51/367 , C07C2601/08 , C07C2601/14 , C07C31/205 , C07C33/46 , C07C31/207 , C07C35/06 , C07C33/26 , C07C31/20 , C07C31/36 , C07C35/14 , C07C43/23
摘要： A carbonyl compound represented by the formula:
wherein A represents C1-7 alkyl or haloalkyl, optionally substituted phenyl, or optionally substituted benzyl; and B represents C1-4 acyl, C1-7 alkoxycarbonyl, haloalkyl, hydroxycarbonyl, C1-7 alkoxyalkyl, hydroxymethyl, optionally substituted benzoyl or C1-7 alkyl-substituted aminomethyl; or A and B with the adjacent C atom form an optionally substituted cyclic 5- or 6-membered 1,2-diketone, is dissolved in amphiprotic solvent and there is added 100-1/50,000 mol of a ruthenium-optically active phosphine derivative as catalyst, e.g. of formula Ru x H y Cl z (R-BINAP)₂-(S) p (III) or [RuH₁(R-BINAP) v ]Y w (V) wherein BINAP is a specific tertiary phosphine group.
The compound (I) is reacted with hydrogen at a pressure of 5-40 kg/cm² for 1-48 hours and there is recovered in high yield as product an optically active alcohol of the formula (II) wherein the =C=O group has become =CH-OH.
摘要翻译：由下式表示的羰基化合物：其中A表示C1-7烷基或卤代烷基，任选取代的苯基或任选取代的苄基; 和B表示C 1-4酰基，C 1-7烷氧基羰基，卤代烷基，羟基羰基，C 1-7烷氧基烷基，羟甲基，任选取代的苯甲酰基或C 1-7烷基取代的氨基甲基; 或具有相邻C原子的A和B形成任选取代的环状5-或6-元1,2-二酮，溶于两性溶剂中，并加入100-1 / 50,000mol钌光学活性膦衍生物作为催化剂，例如式RuxHyClz（R-BINAP）2-（S）p（III）或[RuH1（R-BINAP）v] Yw（Ⅴ）其中BINAP是特定的叔膦基。化合物（I）在5-40kg / cm 2的压力下与氢气反应1-48小时，作为产物以高产率回收式（II）的光学活性醇，其中= C = O组已经成为= CH-OH。

5. 发明公开

EP1300381A1 Process for preparing optically active alcohols 失效
标题翻译：阿尔科伦（Alkoholen）
公开(公告)号：EP1300381A1
公开(公告)日：2003-04-09
申请号：EP02025508.9
申请日：1996-12-06
申请人： JAPAN SCIENCE AND TECHNOLOGY CORPORATION , NKK CORPORATION , Takeda Chemical Industries, Ltd. , Asahi Kasei Kabushiki Kaisha , Takasago International Corporation
发明人： Ikariya, Takao , Hashiguchi, shohei , Takehara, Jun , Uematsu, Nobuyuki , Matsumura, Kazuhiko 203 Okukoto 50-1 , Noyori, Ryoji , Fujii, Akio
IPC分类号： C07B53/00 , C07C29/143 , B01J31/22 , C07F15/00
CPC分类号： B01J31/2295 , B01J31/0237 , B01J31/0239 , B01J31/0252 , B01J31/0267 , B01J31/0271 , B01J31/1805 , B01J2231/643 , B01J2531/821 , C07B2200/07 , C07C29/143 , C07C67/31 , C07C209/52 , C07C213/02 , C07C2601/14 , C07C2602/08 , C07C2602/10 , C07C211/27 , C07C211/30 , C07C211/40 , C07C217/84 , C07C35/32
摘要： The present invention relates to a novel, highly practical method for producing optically active compounds such as optically active alcohol and optically active amine useful for various utilities such as synthetic intermediates of drugs, liquid crystal materials, and optical resolution agents, comprising hydrogen transfer-type asymmetric reduction in the presence of a transition metal catalyst and an optically active nitrogen-containing compound or a transition metal catalyst with an optically active nitrogen-containing compound as the asymmetric ligand, and a hydrogen-donating organic or inorganic compound.
In accordance with the present invention, characteristically, an optically active secondary alcohol can be recovered through the hydrogen transfer-type oxidation from racemic secondary alcohol or meso-type diol.
摘要翻译：本发明涉及一种用于制备光学活性醇和光学活性胺的光学活性化合物的新型高度实用的方法，其可用于各种用途，例如药物，液晶材料和光学拆分剂的合成中间体，包括氢转移型过渡金属催化剂和光学活性含氮化合物或过渡金属催化剂与光学活性含氮化合物作为不对称配体的存在下的不对称还原，以及供氢有机或无机化合物。根据本发明，特征在于可以通过外消旋仲醇或内消旋二醇的氢转移型氧化回收光学活性仲醇。

6. 发明授权

EP0478147B1 Process for producing optically active gamma-butyrolactone derivatives 失效
标题翻译：一种制备光学活性的过程伽玛butyrolactonderivaten
公开(公告)号：EP0478147B1
公开(公告)日：1996-11-06
申请号：EP91307966.1
申请日：1991-08-30
申请人： Takasago International Corporation
发明人： Noyori, Ryoji , Kitamura, Masato , Ohkuma, Takeshi , Sayo, Noboru, c/o Takasago Research Inst. Inc. , Kumobayashi, Hidenori, c/o Takasago Research Inst.
IPC分类号： C07D307/33 , B01J31/00
CPC分类号： B01J31/2404 , B01J31/1805 , B01J31/2208 , B01J31/24 , B01J31/2452 , B01J2231/643 , B01J2531/0216 , B01J2531/0266 , B01J2531/821 , C07D315/00

7. 发明公开

EP0470756A3 Ruthenium-phosphine complex useful as catalyst and intermediate for synthesis thereof 失效
标题翻译：作为催化剂及其合成的中间体的钌 - 磷腈复合物
公开(公告)号：EP0470756A3
公开(公告)日：1993-09-15
申请号：EP91307028.0
申请日：1991-07-31
申请人： Takasago International Corporation
发明人： Noyori, Ryoji , Kitamura, Masato , Sayo, Noboru , Kumobayashi, Hidenori , Giles, Martin F.
IPC分类号： C07F15/00 , B01J31/24
CPC分类号： B01J31/2404 , B01J31/1805 , B01J31/2452 , B01J2231/643 , B01J2531/821 , C07C67/31 , C07F15/0053 , C07C69/675
摘要： A ruthenium-phosphine complex is represented by formula (I) :
wherein R 2- BINAP represents a tertiary phosphine compound represented by formula (II) :
where R 2 is a hydrogen atom or a methyl, methoxy or a t-butyl, X is a halogen atom ; and R and R 1 each represent is an optionally substituted phenyl group, e. g. substituted with alkyl, alkoxy or dialkylamino. A novel rutheniumphosphine complex used as starting material is represented by formula (III) :
wherein R and R 1 are as above and dma represents N,N-dimethylacetamide and is reacted with BINAP in a solvent to make the complex (I). The complex of formula (I) is useful as a catalyst for general organic syntheses with its ligand being an optically inactive compound or for asymmetric syntheses with its ligand being an optically active compound, and can be prepared at a low cost.

8. 发明公开

EP0297752A3 Process of preparing optically active alcohol 失效
标题翻译：制备光学活性醇的方法
公开(公告)号：EP0297752A3
公开(公告)日：1989-03-22
申请号：EP88305462.9
申请日：1988-06-15
申请人： Takasago International Corporation
发明人： Sayo, Noboru , Saito, Takao , Kumobayashi Hidenori , Akutagawa, Susumu , Noyori, Ryoji , Takaya, Hidemasa
IPC分类号： C07C29/136 , C07C31/20 , C07C33/36 , C07C67/31 , C07C41/26 , C07C213/00 , C07C35/06 , C07C31/40 , C07C31/26
CPC分类号： C07C29/145 , C07B2200/07 , C07C41/26 , C07C2601/08 , C07C2601/14 , C07C31/20 , C07C33/26 , C07C35/06 , C07C35/08 , C07C31/42 , C07C43/1785
摘要： A 1,3-diketone (1 mol) of formula:
wherein R¹ and R² each is C1-8 alkyl, haloalkyl, hydroxyalkyl, trifluoromethyl, optionally substituted phenyl-substituted C1-7 alkyl, alkoxycarbonyl-substituted C1-7 alkyl, C1-7 aminoalkyl, a C1-7 alkyl-substituted C1-7 aminoalkyl, optionally substituted phenyl or benzyloxy; R³ is hydrogen, halogen, C1-7 alkyl or C1-8 alkoxycarbonyl; or R¹ or R² and R³ and the C atoms therebetween form a 5- to 7-membered ring which may contain a C1-8 alkoxycarbonyl group or a double bond,
is dissolved in amphiprotic solvent and there is added 100-1/50,000 mol of a ruthenium-optically active phosphine derivative as catalyst, e.g. of formula Ru x H y Cl z (R⁴-BINAP)₂(S) p (III) or [RuH₁(R⁴-BINAP) v ]y w (V) wherein BINAP is a specific tertiary phosphine group. The diketone is reacted with hydrogen at a pressure of 5-100 kg/cm² for 1-48 hours and there is recovered as product an optically active alcohol of the formula (II) wherein the =C=O groups have become =CH-OH, in high yield.
摘要翻译：其中R 1和R 2各自为C 1-8烷基，卤代烷基，羟基烷基，三氟甲基，任选取代的苯基取代的C 1-7烷基，烷氧基羰基，取代的C 1-7烷基，C 1-7氨基烷基，C 1-7烷基取代的C 1-7氨基烷基，任意取代的苯基或苄氧基; R 3是氢，卤素，C 1-7烷基或C 1-8烷氧基羰基; 或R 1或R 2和R 3和它们之间的C原子形成可含有C 1-8烷氧基羰基或双键的5-元至7-元环，溶解于两性溶剂中，加入100-1 / 50,000摩尔的钌 - 光学活性膦衍生物作为催化剂，式RuxHyClz（R 4 -BINAP）2（S）p（III）或[RuH1（R 4 -BINAP）v] yw（V）其中BINAP是特定的叔膦基。二酮与氢气在5-100kg / cm 2的压力下反应1-48小时，作为产物回收作为式（II）的光学活性醇，其中= C = O基团已经变成= CH-OH，产率高。

9. 发明公开

EP0272787A2 Catalytic production of optically active carboxylic acid 失效
标题翻译：卡比利亚产品。
公开(公告)号：EP0272787A2
公开(公告)日：1988-06-29
申请号：EP87310023.4
申请日：1987-11-12
申请人： Takasago International Corporation
发明人： Takaya, Hidemasa , Ohta, Tetsuo , Noyori, Ryoji , Sayo, Noboru , Kumobayashi, Hidenori , Akutagawa, Susumu
IPC分类号： C07C51/36 , C07C53/128 , C07C57/03 , C07C57/30 , C07C57/38 , C07C59/64
CPC分类号： C07F15/0053 , C07C51/36 , C07C53/128 , C07C59/64 , C07C57/03 , C07C57/38 , C07C57/30
摘要： A carboxylic acid having optically active C atom, of formula:
wherein R 1 , R 2 and R 3 each represents hydrogen, alkyl, alkenyl, or phenyl or naphthyl which may have a substituent, provided that all of R 1 to R 3 are not simultaneously hydrogen; when R 1 and R 2 are both hydrogen then R 3 is not methyl and when R 3 is hydrogen, R 1 and R 2 are each other than hydrogen, is produced by dissolving an a,β-unsaturated carboxylic acid represented by the formula:
in an aprotic solvent, optionally adding equimolar tertiary amine and adding a ruthenium-optically active phosphine complex as a catalyst, hydrogenating under pressure of 4-135 kg/cm 2 , and distilling off the solvent.
Three classes of such catalyst, containing a 'BINAP' group, are shown, and syntheses thereof.
The carboxylic acids produced can be used as raw materials for syntheses, e.g. of physiologically active substances of natural materials, and also as liquid crystal materials.
摘要翻译：具有光学活性C原子的具有下式的羧酸：其中R 1，R 2和R 3各自表示可以具有取代基的氢，烷基，链烯基或苯基或萘基，条件是 R 1至R 3全部不同时为氢; 当R 1和R 2都是氢时，R 3不是甲基，当R 3是氢时，R 1和R 2各自是氢，是通过将在非质子溶剂中，任选加入等摩尔叔胺并加入钌光学活性膦配合物作为催化剂，在4-135kg / cm 2的压力下氢化，由式：表示的α，β-不饱和羧酸 >，并蒸除溶剂。显示了三类含有“BINAP”基团的催化剂，并进行了合成。所生成的羧酸可以用作合成的原料，例如。的天然材料的生理活性物质，以及液晶材料。

10. 发明公开

EP1469004A1 Method for preparing aminophosphines and aminophosphine oxides, intermediates therefor 有权
标题翻译： Verfahren zur Herstellung von Aminophosphinen und Aminophosphinoxiden，Zwischenproduktedafür
公开(公告)号：EP1469004A1
公开(公告)日：2004-10-20
申请号：EP04077041.4
申请日：1999-12-23
申请人： Takasago International Corporation
发明人： Sumi, Kenzo , Ikariya, Takao , Noyori, Ryoji
IPC分类号： C07F9/53 , C07F9/50
CPC分类号： C07F15/045 , B01J23/44 , B01J23/468 , B01J31/189 , B01J2231/44 , B01J2231/645 , B01J2531/0266 , B01J2531/821 , B01J2531/822 , B01J2531/824 , B01J2531/827 , B01J2531/847 , C07B53/00 , C07B2200/07 , C07C311/17 , C07F9/5022 , C07F9/5054 , C07F9/509 , C07F9/5325 , C07F15/004 , C07F15/0053 , C07F15/008
摘要： The invention provides a metal complex comprising a ligand and a metal. The ligand is an aminophosphine compound represented by the following formula (1)

[Each Ar represents an aryl group optionally substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atom or an alkoxy group, both Ar's being same or different with each other. R 1 and R 2 represent hydrogen atom, a cycloalkyl group having 5 to 7 carbon atoms, or an alkyl group having 1 to 6 carbon atom optionally substituted with a halogen atom, a lower alkoxy group or phenyl group, with R 1 and R 2 being same or different with each other. Alternatively, one of R 1 and R 2 is hydrogen atom and the other is -COR 3 (R 3 represents a cycloalkyl group having 5 to 7 carbon atoms, a lower alkyl group having 1 to 6 carbon atom optionally substituted with a halogen atom, a lower alkoxy group or phenyl group, a substituted or unsubstituted phenyl group, or a lower alkoxy group having 1 to 6 carbon atom optionally substituted with a cycloalkyl group having 5 to 7 carbon atoms, a halogen atom, a lower alkoxy group or phenyl group) or -SO 2 R 4 (R 4 represents a cycloalkyl group having 5 to 7 carbon atoms, an alkyl group optionally substituted with a halogen atom, a lower alkoxy group or phenyl group, or substituted or unsubstituted phenyl group). n represents 0]. The metal is rhodium, ruthenium, iridium or nickel.
摘要翻译：本发明提供了包含配体和金属的金属络合物。配位体是下式（1）表示的氨基膦化合物。其中，Ar表示可以被卤素原子，碳原子数为1〜4的低级烷基或烷氧基取代的芳基， Ar彼此相同或不同。 R 1和R 2代表氢原子，具有5至7个碳原子的环烷基或具有1-6个碳原子的任选被卤素原子，低级烷氧基或苯基取代的烷基，R 1和R 2彼此相同或不同。或者，R 1和R 2之一是氢原子，另一个是-COR 3（R 3表示具有5至7个碳原子的环烷基，具有1至6个碳原子的低级烷基任选被卤素原子，低级烷氧基或苯基取代的原子，取代或未取代的苯基或任选被具有5至7个碳原子的环烷基取代的具有1至6个碳原子的低级烷氧基，卤素原子，低级烷氧基或苯基）或-SO 2 R 4（R 4表示具有5至7个碳原子的环烷基，任选被卤素原子，低级烷氧基或苯基取代的烷基，或取代或未取代的苯基）。 n表示0Ü。金属是铑，钌，铱或镍。

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