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1. 发明授权

US4739084A Ruthenium-phosphine complex 失效
标题翻译：钌膦络合物
公开(公告)号：US4739084A
公开(公告)日：1988-04-19
申请号：US38570
申请日：1987-04-15
申请人： Hidemasa Takaya , Tetsuo Ohta , Ryoji Noyori , Nobuo Yamada , Toshiyuki Takezawa , Noboru Sayo , Takanao Taketomi , Hidenori Kumobayashi , Susumu Akutagawa
发明人： Hidemasa Takaya , Tetsuo Ohta , Ryoji Noyori , Nobuo Yamada , Toshiyuki Takezawa , Noboru Sayo , Takanao Taketomi , Hidenori Kumobayashi , Susumu Akutagawa
IPC分类号： B01J31/00 , B01J31/24 , C07B61/00 , C07C29/17 , C07C33/025 , C07C51/36 , C07F15/00 , C07F9/50
CPC分类号： C07F15/0053 , C07C29/17 , C07C33/025 , C07C51/36 , C07B2200/07
摘要： 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.
摘要翻译：公开了具有2,2'-双（二苯基膦基）-1,1'-联萘或其衍生物作为配体的钌 - 膦配合物和与其钌原子键合的羧基。该复合物是廉价的并且表现出优异的性能，作为各种有机合成的催化剂，特别是用于不对称氢化。

2. 发明授权

US4962230A Process for producing optically active carboxylic acid 失效
标题翻译：光学活性羧酸的制备方法
公开(公告)号：US4962230A
公开(公告)日：1990-10-09
申请号：US121247
申请日：1987-11-16
申请人： Hidemasa Takaya , Tetsuo Ohta , Ryoji Noyori , Noboru Sayo , Hidenori Kumobayashi , Susumu Akutagawa
发明人： Hidemasa Takaya , Tetsuo Ohta , Ryoji Noyori , Noboru Sayo , Hidenori Kumobayashi , Susumu Akutagawa
IPC分类号： C07C51/36 , C07F15/00
CPC分类号： C07F15/0053 , C07C51/36
摘要： 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.According to the process of the invention, the desired optically active carboxylic acids which can be widely used as raw materials for synthesizing various useful compounds, for example, as intermediates for synthesizing physiologically active substances of natural materials and also as liquid crystal materials can be industrially advantageously produced.

3. 发明授权

US4933482A Process for preparing optically active alcohol 失效
标题翻译：光学活性醇的制备方法
公开(公告)号：US4933482A
公开(公告)日：1990-06-12
申请号：US204480
申请日：1988-06-09
申请人： Noboru Sayo , Takao Saito , Hidenori Kumobayashi , Susumu Akutagawa , Ryoji Noyori , Hidemasa Takaya
发明人： Noboru Sayo , Takao Saito , Hidenori Kumobayashi , Susumu Akutagawa , Ryoji Noyori , Hidemasa Takaya
IPC分类号： C07C67/303 , B01J31/24 , C07B31/00 , C07B53/00 , C07B61/00 , C07C67/00 , C07C67/31 , C07C69/675 , C07C69/757 , C07C227/00 , C07C227/16 , C07C227/32 , C07C229/22 , C07C229/24 , C07C231/00 , C07C231/12 , C07C231/18 , C07C235/06 , C07C235/34 , C07C237/06 , C07C325/00 , C07C327/22
CPC分类号： C07C227/32 , C07C323/00
摘要： 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.

4. 发明授权

US4962242A Process for producing optically active alcohols 失效
标题翻译：光学活性醇的制造方法
公开(公告)号：US4962242A
公开(公告)日：1990-10-09
申请号：US66164
申请日：1987-06-25
申请人： Nobuo Yamada , Toshiyuki Takezawa , Noboru Sayo , Misao Yagi , Hidenori Kumobayashi , Susumu Akutagawa , Hidemasa Takaya , Shinichi Inoue , Ryoji Noyori
发明人： Nobuo Yamada , Toshiyuki Takezawa , Noboru Sayo , Misao Yagi , Hidenori Kumobayashi , Susumu Akutagawa , Hidemasa Takaya , Shinichi Inoue , Ryoji Noyori
IPC分类号： C07C29/17
CPC分类号： C07C29/172 , C07B2200/07
摘要： 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.
摘要翻译：一种制备由式（I）表示的光学活性醇的方法：其中R1是具有2至11个碳原子的烷基，具有3至11个碳原子的链烯基，具有环己基，环己基甲基或环己基乙基，条件是烯基或链二烯基中的烯烃在2-位没有与烯烃共轭; 和*表示不对称碳原子，包括使式（II）表示的烯属醇：其中R 1与上述定义相同，在作为催化剂的存在下进行不对称氢化钌 - 光学活性膦配合物。根据本发明的方法，不仅可用于制造香料和维生素E，而且用作液晶材料的中间体所需的光学活性醇可以以高光学纯度生产。

5. 发明授权

US4916252A Process for preparing optically active alcohol 失效
公开(公告)号：US4916252A
公开(公告)日：1990-04-10
申请号：US207428
申请日：1988-06-16
申请人： Noboru Sayo , Takao Saito , Hidenori Kumobayashi , Susumu Akutagawa , Ryoji Noyori , Hidemasa Takaya
发明人： Noboru Sayo , Takao Saito , Hidenori Kumobayashi , Susumu Akutagawa , Ryoji Noyori , Hidemasa Takaya
IPC分类号： B01J31/24 , C07B31/00 , C07B41/02 , C07B53/00 , C07B61/00 , C07C27/00 , C07C29/145 , C07C31/20 , C07C31/42 , C07C33/26 , C07C33/46 , C07C35/06 , C07C41/00 , C07C41/26 , C07C43/178 , C07C67/00 , C07C67/31 , C07C69/675 , C07C69/738 , C07C213/00 , C07C215/18 , C07F15/00
CPC分类号： C07C29/145 , C07C41/26 , C07B2200/07 , C07C2101/08 , C07C2101/14
摘要： 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.

6. 发明授权

US4739085A Ruthenium-phosphine complex 失效
标题翻译：钌膦络合物
公开(公告)号：US4739085A
公开(公告)日：1988-04-19
申请号：US61770
申请日：1987-06-15
申请人： Hidemasa Takaya , Tetsuo Ohta , Ryoli Noyori , Noboru Sayo , Hidenori Kumobayashi , Susumu Akutagawa
发明人： Hidemasa Takaya , Tetsuo Ohta , Ryoli Noyori , Noboru Sayo , Hidenori Kumobayashi , Susumu Akutagawa
IPC分类号： B01J31/00 , B01J31/24 , C07B61/00 , C07C29/17 , C07C51/36 , C07F15/00 , C07F9/50
CPC分类号： C07C51/36 , C07C29/17 , C07F15/0053 , C07B2200/07
摘要： 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.
摘要翻译：由式（I）表示的钌膦络合物：[RuH1（R-BINAP）m] Xn'（I）其中R-BINAP是由式（II）表示的叔膦：其中R是氢原子或甲基; X是ClO4，BF4或PF6; 当l为0时，m为1，n'为2，当l为1时，m为2，n'为1。该复合物是廉价的并且表现出优异的性能，作为各种有机合成的催化剂，特别是用于不对称氢化。

7. 发明授权

US5066815A Process for 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：US5066815A
公开(公告)日：1991-11-19
申请号：US520149
申请日：1990-05-08
申请人： Noboru Sayo , Hidenori Kumobayashi , Susumo Akutagawa , Ryoji Noyori , Hidemasa Takaya
发明人： Noboru Sayo , Hidenori Kumobayashi , Susumo Akutagawa , Ryoji Noyori , Hidemasa Takaya
IPC分类号： C07D307/33 , B01J31/24 , C07B31/00 , C07B41/02 , C07B53/00 , C07B61/00 , C07C27/00 , C07C29/145 , C07C31/20 , C07C31/36 , C07C33/26 , C07C35/06 , C07C35/08 , C07C41/00 , C07C41/26 , C07C43/13 , C07C43/178 , C07C51/00 , C07C51/367 , C07C59/01 , C07C59/50 , C07C67/00 , C07C67/31 , C07C213/00 , C07C215/08
CPC分类号： C07C29/145 , C07C41/26 , C07C51/367 , C07B2200/07 , C07C2101/08 , C07C2101/14
摘要： 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.

8. 发明授权

US4851537A Process for preparing N-acyltetrahydroisoquinoline 失效
标题翻译：制备N-酰基四氢异喹啉的方法
公开(公告)号：US4851537A
公开(公告)日：1989-07-25
申请号：US38571
申请日：1987-04-15
申请人： Ryoji Noyori , Masato Kitamura , Hidemasa Takaya , Hidenori Kumobayashi , Susumu Akutagawa
发明人： Ryoji Noyori , Masato Kitamura , Hidemasa Takaya , Hidenori Kumobayashi , Susumu Akutagawa
IPC分类号： C07B61/00 , B01J31/00 , B01J31/24 , C07D217/06 , C07D217/20
CPC分类号： C07D217/06 , C07D217/20
摘要： A process for preparing an N-acyltetrahydroisoquinoline represented by formula (II) ##STR1## wherein A represents a phenylene ring substituted with a hydroxyl group, a lower alkoxy group, an acetoxy group, or a benzyloxy group; R represents a hydrogen atom, a lower alkyl group, or a phenyl group; and X represents a hydrogen atoms, a phenyl group, or a phenyl group substituted with a hydroxyl group, a lower alkoxy group, or an acetoxy group, which comprises asymmetrically hydrogenating an N-acyl-1-methylenetetrahydroisoquinoline or N-acyl-1-benzylidenetetrahydroisoquinoline represented by formula (I) ##STR2## wherein A, R, and X are as defined above, in the presence of an optically active ruthenium-phosphine complex as a catalyst. The process exclusively and efficiently provides a useful isomer of the N-acyltetrahydroisoquinoline of high purity which is useful as an intermediate for synthesizing isoquinoline type alkaloids as pharmaceuticals without involving optical resolution of a racemate.
摘要翻译：制备由式（II）表示的N-酰基四氢异喹啉的方法其中A表示被羟基，低级烷氧基，乙酰氧基或苄氧基取代的亚苯基环; R表示氢原子，低级烷基或苯基; X表示氢原子，苯基或被羟基，低级烷氧基或乙酰氧基取代的苯基，其包括不对称地氢化N-酰基-1-亚甲基四氢异喹啉或N-酰基-1- 由式（I）表示的亚苄基四氢异喹啉，其中A，R和X如上所定义，在光学活性钌 - 膦配合物作为催化剂存在下进行。该方法专门有效地提供了高纯度的N-酰基四氢异喹啉的有用异构体，其可用作合成异喹啉类生物碱作为药物而不涉及外消旋物的光学拆分的中间体。

9. 发明授权

US5563295A Process for producing optically active carboxylic acid 失效
标题翻译：光学活性羧酸的制备方法
公开(公告)号：US5563295A
公开(公告)日：1996-10-08
申请号：US399549
申请日：1995-03-07
申请人： Hidemasa Takaya , Xiaoyong Zhang , Kazuhiko Matsumura , Noboru Sayo , Hidenori Kumobayashi
发明人： Hidemasa Takaya , Xiaoyong Zhang , Kazuhiko Matsumura , Noboru Sayo , Hidenori Kumobayashi
IPC分类号： B01J31/24 , C07B53/00 , C07B61/00 , C07C51/36 , C07C53/126 , C07C53/128 , C07C57/30 , C07F9/50
CPC分类号： C07C51/36 , C07B53/00 , C07F9/5027
摘要： A process for the production of an optically active carboxylic acid (I), which comprises subjecting an olefinic carboxylic acid (II) to asymmetric hydrogenation using a complex as a catalyst consisting of an optically active phosphine (III) and a ruthenium compound.Complex of ##STR1## with a ruthenium compound ##STR2## According to the process of the present invention, optically active carboxylic acids can be produced with high yield.
摘要翻译：一种制备光学活性羧酸（I）的方法，其包括使用络合物作为由光学活性膦（III）和钌化合物组成的催化剂使烯属羧酸（II）进行不对称氢化。＆lt; IMAGE＆gt;与钌化合物的复合物＆lt; IMAGE＆gt;根据本发明的方法，可以高产率制备光学活性羧酸。

10. 发明授权

US4994590A Ruthenium-phoshine complex 失效
标题翻译：钌 - 磷光复合物
公开(公告)号：US4994590A
公开(公告)日：1991-02-19
申请号：US427209
申请日：1989-10-24
申请人： Hidemasa Takaya , Kazushi Mashima , Hidenori Kumobayashi , Noboru Sayo
发明人： Hidemasa Takaya , Kazushi Mashima , Hidenori Kumobayashi , Noboru Sayo
IPC分类号： B01J31/24 , C07B61/00 , C07C51/36 , C07C67/31 , C07C69/675 , C07F15/00 , C07F9/50
CPC分类号： B01J31/2452 , C07C51/36 , C07C67/31 , C07F15/0053 , B01J2231/641 , B01J2231/643 , B01J2531/0266 , B01J2531/821
摘要： 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.

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