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1. 发明授权

EP0732350B1 Process for producing optically active polyketone 失效
标题翻译：一种用于光学活性的聚酮的制备方法
公开(公告)号：EP0732350B1
公开(公告)日：1999-06-02
申请号：EP96301719.9
申请日：1996-03-13
申请人： Takasago International Corporation
发明人： Takaya, Hidemasa , Tamoa, Kyoko, Beru Mezon Kamogawa 201 , Sato, Naomasa
IPC分类号： C08G67/02
CPC分类号： C08G67/02 , C07F9/65744

2. 发明公开

EP0408340A3 Ruthenium-optically active phoshine complex useful as catalyst 失效
标题翻译：作为催化剂的红外光活性酚类复合物
公开(公告)号：EP0408340A3
公开(公告)日：1991-07-03
申请号：EP90307585.1
申请日：1990-07-11
申请人： Takasago International Corporation
发明人： Nohira, Hiroyuki , Takaya, Hidemasa , Miyashita, Akira
IPC分类号： C07F15/00 , B01J31/24 , C07B53/00 , C07C51/36 , C07C67/303
CPC分类号： C07C51/36 , C07C201/12 , C07C209/36 , C07C209/62 , C07C231/02 , C07F9/5027 , C07F15/0053 , C07C233/15 , C07C211/52 , C07C211/50 , C07C205/06 , C07C205/12
摘要： A ruthenium-optically active phosphine complex has, as a ligand, BICHEP, i.e., 2,2′-bis(dicyclohexyl-phosphino)-6,6′ dimethyl-1,1′-biphenyl represented by formula (I):
Specific examples of the complex are:
[Ru(BICHEP](OAc)₂ (wherein Ac is an acetyl group)
[Ru(BICHEP)(p-cymene)I]I
[Ru(BICHEP)(p-cymene)Cl]Cl
(Ru₂Cl₄(BICHEP)₂]NEt₃ (wherein Et is an ethyl group). Preparation is by the processes of US-4739084, EP-A-366,390 and US-4691037. Preparation of optically active BICHEP is described. The complex is used to catalyse assymmetric syntheses, e.g. of an optically active carboxylic acid or ester in high purity and good yield.

3. 发明公开

EP0366390A3 Ruthenium-phosphine complexes 失效
标题翻译：钌 - 膦配合物
公开(公告)号：EP0366390A3
公开(公告)日：1990-07-04
申请号：EP89310901.7
申请日：1989-10-23
申请人： Takasago International Corporation
发明人： Takaya, Hidemasa , Mashima, Kazushi , Kumobayashi, Hidenori , Sayo, Noboru
IPC分类号： C07F15/00 , C07B53/00 , C07C67/31
CPC分类号： B01J31/2452 , B01J2231/641 , B01J2231/643 , B01J2531/0266 , B01J2531/821 , C07C51/36 , C07C67/31 , C07F15/0053
摘要： A ruthenium-phosphine complex is of formula
[RUX ℓ (L) m (R-BINAP)]Y n (I)
wherein R-BINAP represents a tertiary phosphine represented by
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, ClO₄, PF₆, BPh₄ (wherein Ph represents a phenyl group) or BF₄; when L is substituted or unsubstituted benzene, ℓ represents 1, m represents 1, and n represents 1; and when L is acetonitrile, when ℓ is 1, then m represents 2, and n represents 1, and when ℓ is 0, then m represents 4, and n represents 2. 27 specific complexes are shown. Synthesis is by
(a) RuCl₂(Ar) + BINAP in a solvent at 25 to 50°C; (b) [RuCl₂ (Ar)]₂ + Br or I salt of Li, Na or K, in water or in a mixture of water and methylene chloride and in presence of a quaternary ammonium or phosphonium halide; (c) [RuCl(Ar) BINAP]Cl + a Na, K, Li, Mg or Ag salt (MY); of ClO₄, PF₆ BPh₄ or BF ₄ , in an organic solvent; or (d) [RuCl(Ar) BINAP]Cl in an organic solvent, optionally with MY is heated at 25°C-50°C for 10-24 hours. The complex is used as catalyst in asymmetric hydrogenation, e.g. of methyl acetoacetate, and exhibits excellent catalytic activity to provide a product of high optical purity.
摘要翻译：钌 - 膦配合物具有式[RUXl（L）m（R-BINAP）] Yn（I）其中R-BINAP代表叔膦，其中R代表氢原子或甲基; X代表卤素原子; L表示取代或未取代的苯或乙腈; Y代表卤原子，ClO 4，PF 6，BPh 4（其中Ph代表苯基）或BF 4; 当L是取代或未取代的苯时，l代表1，m代表1，n代表1; 当L为乙腈时，当l为1时，m代表2，n代表1，当l为0时，m代表4，n代表2.27个特定的配合物。合成通过（a）RuCl 2（Ar）+ BINAP在25-50℃的溶剂中进行; （b）在水中或在水和二氯甲烷的混合物中，在季铵或卤化鏻存在下，[RuCl 2（Ar）] 2 + Br或I的Li，Na或K的盐; （c）[RuCl（Ar）BINAP] Cl + Na，K，Li，Mg或Ag盐（MY）; ClO 4，PF 6 BPh 4或BF 4在有机溶剂中的溶液; 或（d）[RuCl（Ar）BINAP] Cl在有机溶剂中，任选与MY在25℃-50℃加热10-24小时。该配合物在不对称氢化中用作催化剂，例如，的乙酰乙酸甲酯，并且表现出优异的催化活性以提供高光学纯度的产物。

4. 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。

5. 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。

6. 发明公开

EP0732350A3 Process for producing optically active polyketone 失效
标题翻译：一种用于光学活性的聚酮的制备方法
公开(公告)号：EP0732350A3
公开(公告)日：1997-07-30
申请号：EP96301719.9
申请日：1996-03-13
申请人： Takasago International Corporation
发明人： Takaya, Hidemasa , Tamoa, Kyoko, Beru Mezon Kamogawa 201 , Sato, Naomasa
IPC分类号： C08G67/02
CPC分类号： C08G67/02 , C07F9/65744
摘要： A process for producing optically active polyketone which comprises allowing a mono-substituted ethylene to react with carbon monoxide in the presence of a palladium-phosphine complex formed from a phosphine represented by the following general formula (I)

(wherein Ar 1 is a phenyl group which may be substituted with one or more substituent groups selected from a lower alkyl group, a lower alkoxy group and a halogen) and a palladium salt. An isotactic (stereoregular) optically active polyketone having high molecular weight (Mn) in which the direction of a mono-substituted ethylene against ketone is a head to tail type (positional regularity) can be produced efficiently by a simple and easy process for the copolymerization of propylene, styrene or the like mono-substituted ethylene with carbon monoxide.

8. 发明公开

EP0614870A2 Process for producing optically active aldehydes 失效
标题翻译：阿尔多芬。
公开(公告)号：EP0614870A2
公开(公告)日：1994-09-14
申请号：EP94103675.8
申请日：1994-03-10
申请人： MITSUBISHI GAS CHEMICAL COMPANY, INC. , Takasago International Corporation
发明人： Takaya, Hidemasa , Sakai, Nozomu , Tamao, Kyoko, Beru Mezon Kamogawa 303 , Mano, Satoshi , Kumobayashi, Hidenori, c/o Takasago Int. Corp. , Tomita, Tetsuo
IPC分类号： C07C45/50 , C07C45/49 , C07C47/14 , C07C47/228 , C07C47/277 , C07C67/293 , C07C69/14 , C07D209/48 , C07C253/30 , C07C255/17
CPC分类号： C07D209/48 , C07C45/49 , C07C45/505 , C07C51/235 , C07C51/487 , C07C67/293 , C07C221/00 , C07C231/12 , C07C253/30 , C07F9/5022 , C07C69/14
摘要： Disclosed herein is a process for producing an optically active aldehyde represented by the following formula (2):

OHC-CH(CH₃)-Q (2)

wherein Q means a halogen atom, lower alkyl group, phthalimide group, lower alkylcarbonyloxy group, cyano group, carboxyl group, lower alkyloxycarbonyl group, lower alkoxy group, lower alkylcarbonyl group, acetylamino group, benzoylamino group, monoalkylamino group, dialkylamino group, benzoyl group, phenyl group which may be substituted by a halogen atom, lower alkyl group or lower alkoxy group, or naphthyl group which may be substituted by a halogen atom, lower alkyl group or lower alkoxy group, which comprises hydroformylating a vinyl compound represented by the following formula (1):

CH₂=CH-Q (1)

wherein Q has the same meaning as defined above, using a specific rhodium-phosphine complex as a catalyst. According to the process, optically active aldehydes which require much labor and time to synthesize, and are expensive can be produced at a high yield and a low cost by a simple process under mild conditions.
摘要翻译：本文公开了一种由下式（2）表示的光学活性醛的制备方法：OHC-CH（CH3）-Q（2）其中Q表示卤素原子，低级烷基，邻苯二甲酰亚胺基，低级烷基羰基氧基，氰基羧基，低级烷氧基羰基，低级烷氧基，低级烷基羰基，乙酰氨基，苯甲酰氨基，一烷基氨基，二烷基氨基，苯甲酰基，可被卤素原子取代的苯基，低级烷基或低级烷氧基，或可以被卤素原子，低级烷基或低级烷氧基取代的萘基，其包括将由下式（1）表示的乙烯基化合物加氢甲酰化：CH 2 = CH-Q（1）其中Q具有相同的含义如上所述，使用特定的铑 - 膦配合物作为催化剂，根据该方法，可以高产率生产需要大量劳动和合成时间并且昂贵的光学活性醛并且在温和条件下通过简单的方法成本低。

9. 发明授权

EP0366390B1 Ruthenium-phosphine complexes 失效
标题翻译：钌膦络合物。
公开(公告)号：EP0366390B1
公开(公告)日：1994-01-19
申请号：EP89310901.7
申请日：1989-10-23
申请人： Takasago International Corporation
发明人： Takaya, Hidemasa , Mashima, Kazushi , Kumobayashi, Hidenori , Sayo, Noboru
IPC分类号： C07F15/00 , C07B53/00 , C07C67/31
CPC分类号： B01J31/2452 , B01J2231/641 , B01J2231/643 , B01J2531/0266 , B01J2531/821 , C07C51/36 , C07C67/31 , C07F15/0053

10. 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。

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