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1. 发明授权

US4981992A Process for preparing optically active 3-hydroxybutanoic acid 失效
标题翻译：制备光学活性3-羟基丁酸的方法
公开(公告)号：US4981992A
公开(公告)日：1991-01-01
申请号：US435877
申请日：1989-11-14
申请人： Noboru Sayo , Takao Saito , Yoshiki Okeda , Hiroyuki Nagashima , Hidonori Kumobayashi
发明人： Noboru Sayo , Takao Saito , Yoshiki Okeda , Hiroyuki Nagashima , Hidonori Kumobayashi
IPC分类号： B01J31/24 , C07B53/00 , C07B61/00 , C07C231/18 , C07C233/47 , C07C233/83 , C07C235/52 , C07C269/06 , C07C271/22 , C07D205/08
CPC分类号： C07C231/18 , C07C233/47 , C07C233/83 , C07C269/06 , C07C271/22 , C07D205/08 , Y02P20/55
摘要： 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.

2. 发明授权

US5144042A Process for preparing optically active 3-hydroxypyrrolidine derivatives 失效
标题翻译：制备光学活性3-羟基吡咯烷衍生物的方法
公开(公告)号：US5144042A
公开(公告)日：1992-09-01
申请号：US682273
申请日：1991-04-09
申请人： Nobuo Seido , Yoshiki Okeda , Hidenori Kumobayashi
发明人： Nobuo Seido , Yoshiki Okeda , Hidenori Kumobayashi
IPC分类号： C07B53/00 , C07C31/34 , C07C211/27 , C07C309/65 , C07C309/73 , C07D207/12
CPC分类号： C07D207/12
摘要： A process for preparing optically active 3-hydroxypyrrolidine derivatives useful as intermediates represented by formula (III): ##STR1## wherein Q represents a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, comprising reacting an optically active 4-halo-3-hydroxybutane derivative represented by formula (I): ##STR2## wherein * is as defined above; R.sup.1 represents a lower alkyl group or a substituted or unsubstituted phenyl group; and X represents a halogen atom, with a benzylamine derivative represented by formula (II):H.sub.2 NCH.sub.2 Q (II)wherein Q is as defined above, is disclosed. The starting compound (I) is easily available through chemical synthesis. Any complicated procedure or use of an expensive reagent is not required.

3. 发明授权

US6043380A Ruthenium-I0D0-optically active phosphine complex 失效
标题翻译：钌-I0D0-光学活性膦配合物
公开(公告)号：US6043380A
公开(公告)日：2000-03-28
申请号：US307750
申请日：1999-05-10
申请人： Yoshiki Okeda , Tsutomu Hashimoto , Yoji Hori , Toshimitsu Hagiwara
发明人： Yoshiki Okeda , Tsutomu Hashimoto , Yoji Hori , Toshimitsu Hagiwara
IPC分类号： B01J31/24 , C07D315/00 , C07F15/00 , C07F9/02 , C07D305/00
CPC分类号： B01J31/2409 , B01J31/2452 , B01J31/2457 , C07D315/00 , C07F15/0053 , B01J2231/645 , B01J2531/0266 , B01J2531/821
摘要： This invention is concerned with a ruthenium-iodo-optically active bidentate phosphine complex of the formula (I):[Ru--(I).sub.q --(T.sup.1).sub.n (SOL).sub.r (L)].sub.m (T.sup.2).sub.p (I).sub.s (I)wherein T.sup.1 represents a carboxylic acid anion, SOL represents a polar solvent, L represents an optically active bidentate phosphine ligand, T.sup.2 represents an anion different from halogen atom anions and carboxylic acid anions, n denotes 0 or 1, r denotes 0, 3 or 4, m denotes 1 or 2, q denotes 0 or 1, or where m is 2, q may represent 1 or 1.5, p denotes 0 or 1, and s denotes 0, 1 or 2 is prepared. Said phosphine complex is usefull as an efficient catalyst for asymmetrically hydrogenating 4-methylene-2-oxetanone into optically active 4-methyl-2-oxetanone.
摘要翻译：本发明涉及式（I）的钌 - 碘 - 光学活性二齿膦络合物：[Ru-（I）q-（T1）n（SOL）r（L）] m（T2）p（I） s（I）其中T1表示羧酸阴离子，SOL表示极性溶剂，L表示光学活性二齿膦配体，T2表示不同于卤素阴离子和羧酸阴离子的阴离子，n表示0或1，r表示0 3或4，m表示1或2，q表示0或1，或其中m为2，q可以表示1或1.5，p表示0或1，s表示0,1或2。所述膦配合物可用作用于将4-亚甲基-2-氧杂环丁酮不对称氢化成光学活性的4-甲基-2-氧杂环丁酮的有效催化剂。

4. 发明授权

US06570035B2 Process for producing pivaloyl-acetic acid ester 失效
标题翻译：生产新戊酰乙酸酯的方法
公开(公告)号：US06570035B2
公开(公告)日：2003-05-27
申请号：US09759134
申请日：2001-01-16
申请人： Shinya Yamada , Yoshiki Okeda , Toshimitsu Hagiwara , Akio Tachikawa , Kouji Ishiguro , Shunichi Harada
发明人： Shinya Yamada , Yoshiki Okeda , Toshimitsu Hagiwara , Akio Tachikawa , Kouji Ishiguro , Shunichi Harada
IPC分类号： C07C6966
CPC分类号： C07C67/343 , C07C69/716
摘要： A process for producing a pivaloylacetic acid ester comprises reacting pivaloyl chloride with an acetoacetic acid ester of an alkyl group having 1 to 4 carbon atoms in the presence of at least one nitrogen-containing basic compound (a) selected from among pyridine compounds, N,N-dialkylanilines and imidazole compounds and from 0.01 to 0.5 mole equivalent, based on the pivaloyl chloride, of a magnesium compound (b) to thereby prepare a pivaloylacetoacetic acid ester and then alcholyzing or alkali-hydrolyzing the pivaloylacetoacetic acid ester to thereby give a pivaloylacetic acid ester having a high purity at a low cost.
摘要翻译：一种生产新戊酰乙酸酯的方法，包括在至少一种选自吡啶化合物，N，N-二甲基甲酰胺的含氮碱性化合物（a）的存在下，使新戊酰氯与具有1至4个碳原子的烷基的乙酰乙酸酯反应， N-二烷基苯胺和咪唑化合物，和基于新戊酰氯的0.01至0.5摩尔当量的镁化合物（b），从而制备新戊酰乙酰乙酸酯，然后将新戊酰乙酰乙酸酯进行共沸或碱解水解，从而得到新戊酰乙酸酸酯以低成本具有高纯度。

5. 发明授权

US06486353B2 Process for producing optically active 3,7-dimethyl-6-octenol and process for producing intermediate therefor 失效
标题翻译：光学活性3,7-二甲基-6-辛烯醇的制备方法及其制备方法
公开(公告)号：US06486353B2
公开(公告)日：2002-11-26
申请号：US10098358
申请日：2002-03-18
申请人： Shinya Yamada , Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
发明人： Shinya Yamada , Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
IPC分类号： C07C20960
CPC分类号： C07C209/68 , C07B2200/07 , C07C29/141 , C07C33/025 , C07C45/42 , C07C47/21 , C07C211/21
摘要： Cis-3,7-dimethyl-2,7-octadienylamine containing from 2 to 10% by weight cis-3,7-dimethyl-2,7-octadienylamine is prepared by subjecting a mixture of an alkylamine and isoprene in a molar ratio of 1:4 to 1:4.5 to telomerization at 80 to 100° C. for from 2.5 to 3.5 hours in the presence of an alkyllithium catalyst and/or phenyllithium catalyst.
摘要翻译：含有2〜10重量％顺式-3,7-二甲基-2,7-辛二烯基的顺式-3,7-二甲基-2,7-辛二烯胺是通过使烷基胺和异戊二烯的混合物以 1：4至1：4.5以在烷基锂催化剂和/或苯基锂催化剂存在下在80至100℃下调聚2.5至3.5小时。

6. 发明授权

US5981771A Ruthenium-optically active phosphine complex, process for the preparation thereof and process for the preparation of optically active 4-methyl-2-oxetanone using same 失效
标题翻译：钌光学活性膦络合物，其制备方法和使用其制备光学活性4-甲基-2-氧杂环丁酮的方法
公开(公告)号：US5981771A
公开(公告)日：1999-11-09
申请号：US100755
申请日：1998-06-22
申请人： Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
发明人： Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
IPC分类号： C07D305/12 , B01J31/24 , C07B53/00 , C07B61/00 , C07D315/00 , C07F15/00
CPC分类号： B01J31/2452 , C07D315/00 , C07F15/0053 , B01J2231/645 , B01J2531/0266 , B01J2531/821 , B01J31/2208 , B01J31/2295 , C07B2200/07
摘要： The present invention provides a catalyst which exhibits a high catalytic activity and allows asymmetric reaction in a high asymmetric yield to obtain a reaction product having a high optical purity. The present invention also provides a process for the preparation of an optically active 4-methyl-2-oxetanone having a high optical purity useful as starting material of polymer in a high yield in a short period in the presence of the foregoing catalyst. A novel ruthenium-iodo-optically active phosphine complex is provided, represented by the following general formula (1):Ru--I.sub.2 -(R.sup.1 -BINAP) (1)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by the following general formula (2): ##STR1## wherein R.sup.1 represents an aryl group which may have a substituent selected from the group consisting of a C.sub.1-4 lower alkyl group, a C.sub.1-4 lower alkoxy group, a C.sub.1-4 lower alkylamino group, and a halogen atom or a C.sub.3-8 cycloalkyl group.
摘要翻译：本发明提供一种催化活性高的催化剂，能够以不对称产率进行不对称反应，得到光学纯度高的反应产物。本发明还提供了在上述催化剂存在下，在短时间内以高收率制备具有高光学纯度的光学纯度高的光学活性4-甲基-2-氧杂环丁酮的方法。提供了由以下通式（1）表示的新型钌 - 碘 - 光学活性膦配合物：Ru-I2-（R1-BINAP）（1）其中R1-BINAP表示由以下通式表示的光学活性叔膦式（2）：其中R1表示可以具有选自C 1-4低级烷基，C 1-4低级烷氧基，C 1-4低级烷基氨基和卤素原子的取代基的芳基或C 3-8环烷基。

7. 发明授权

US5412109A Process for preparing optically active 4-methyl-2-oxetanone 失效
标题翻译：制备光学活性4-甲基-2-氧杂环丁酮的方法
公开(公告)号：US5412109A
公开(公告)日：1995-05-02
申请号：US159262
申请日：1993-11-30
申请人： Hidemasa Takaya , Tetsuo Ohta , Hidenori Kumobayashi , Yoshiki Okeda , Yoshiharu Gonda
发明人： Hidemasa Takaya , Tetsuo Ohta , Hidenori Kumobayashi , Yoshiki Okeda , Yoshiharu Gonda
IPC分类号： C07D315/00 , C07F15/00 , C07D305/06
CPC分类号： C07D315/00 , C07F15/0053
摘要： A process for preparing optically active 4-methyl-2-oxetanone which comprises asymmetrically hydrogenating 4-methylene-2-oxetanone in the presence of a ruthenium-optically active phosphine complex. Optically active 4-methyl-2-oxetanone can easily and economically be obtained at high optical purity.
摘要翻译：制备光学活性4-甲基-2-氧杂环丁酮的方法，其包括在钌 - 光学活性膦配合物存在下不对称氢化4-亚甲基-2-氧杂环丁酮。在高光学纯度下，可以容易且经济地获得光学活性的4-甲基-2-氧杂环丁酮。

8. 发明授权

US06774269B2 Process for producing isopulegol 失效
标题翻译：异丙醇的制备方法
公开(公告)号：US06774269B2
公开(公告)日：2004-08-10
申请号：US10045157
申请日：2002-01-15
申请人： Takeshi Iwata , Yoshiki Okeda , Yoji Hori
发明人： Takeshi Iwata , Yoshiki Okeda , Yoji Hori
IPC分类号： C07C3508
CPC分类号： C07C29/56 , C07C2601/14 , C07C35/17
摘要： A process for producing l-isopulegol by simple operations with safety in high yield. A process for producing isopulegol, which comprises selectively cyclizing citronellal in the presence of a tris(2,6-diarylphenoxy)aluminum catalyst represented by the following general formula (3): wherein Al represents an aluminum atom, Ar1 and Ar2 each represent a substituted or unsubstituted aryl group or a heteroaryl group; and R1, R2 and R3 each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atom(s), an alkoxy group having 1 to 8 carbon atom(s), a substituted or unsubstituted aryl group, a dialkylamino group having 1 to 4 carbon atom(s), or a nitro group.
摘要翻译：通过简单的操作以高产率安全地生产l-异头孢烯的方法。一种生产异胡醇的方法，其包括在由以下通式（3）表示的三（2,6-二芳基苯氧基）铝催化剂存在下选择性环化香茅醛：其中Al表示铝原子，Ar 1和Ar 2， 2>各自表示取代或未取代的芳基或杂芳基; R 1，R 2和R 3各自表示氢原子，卤素原子，碳原子数为1〜8的烷基，碳原子数1〜8的烷氧基，取代或未取代的芳基，碳原子数为1〜4的二烷基氨基或硝基。

9. 发明授权

US06489522B2 Process for producing optically active 3,7-dimethyl-6-octenol and process for producing intermediate therefor 失效
标题翻译：光学活性3,7-二甲基-6-辛烯醇的制备方法及其制备方法
公开(公告)号：US06489522B2
公开(公告)日：2002-12-03
申请号：US09827334
申请日：2001-04-06
申请人： Shinya Yamada , Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
发明人： Shinya Yamada , Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
IPC分类号： C07C3500
CPC分类号： C07C209/68 , C07B2200/07 , C07C29/141 , C07C33/025 , C07C45/42 , C07C47/21 , C07C211/21
摘要： Provided is citronellol, which has an elegant rosy fragrance and is extremely useful for fragrance impartation to aromatic articles. A mixture of an alkylamine and isoprene in a molar ratio of from 1:4 to 1:4.5 is subjected to telomerization at 80 to 100° C. for 2.5 to 3.5 hours in the presence of an alkyllithium catalyst and/or phenyllithium catalyst to obtain a nerylamine compound containing 2 to 10 wt % &agr;-nerylamine compound represented by general formula (4). From this nerylamine compound, citronellol containing 2 to 10 wt % optically active 3,7-dimethyl-7-octenol is produced through the reaction steps of asymmetric isomerization, hydrolysis, and hydrogenation.
摘要翻译：提供香茅醇，其具有优雅的玫瑰香，并且对芳香物品的芳香赋予非常有用。摩尔比为1:4〜1:4.5的烷基胺和异戊二烯的混合物在烷基锂催化剂和/或苯基锂催化剂存在下，在80〜100℃下进行2.5〜3.5小时的调聚，得到含有通式（4）表示的2-10重量％α-椰子胺化合物的橙花胺化合物。由该橙花胺化合物，通过反应步骤产生含有2至10重量％光学活性的3,7-二甲基-7-辛烯醇的香茅醇的不对称异构化，水解和氢化。

10. 发明授权

US5981782A Ruthenium-optically active phosphine complex, process for the preparation thereof and process for the preparation of optically active 4-methyl-2-oxetanone using same 失效
标题翻译：钌光学活性膦络合物，其制备方法和使用其制备光学活性4-甲基-2-氧杂环丁酮的方法
公开(公告)号：US5981782A
公开(公告)日：1999-11-09
申请号：US963619
申请日：1997-11-04
申请人： Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
发明人： Yoshiki Okeda , Yoji Hori , Toshimitsu Hagiwara
IPC分类号： C07D305/12 , B01J31/24 , C07B53/00 , C07B61/00 , C07D315/00 , C07F15/00
CPC分类号： B01J31/2452 , C07D315/00 , C07F15/0053 , B01J2231/645 , B01J2531/0266 , B01J2531/821 , B01J31/2208 , B01J31/2295 , C07B2200/07
摘要： The present invention provides a catalyst which exhibits a high catalytic activity and allows asymmetric reaction in a high asymmetric yield to obtain a reaction product having a high optical purity. The present invention also provides a process for the preparation of an optically active 4-methyl-2-oxetanone having a high optical purity useful as starting material of polymer in a high yield in a short period in the presence of the foregoing catalyst. A novel ruthenium-iodo-optically active phosphine complex is provided, represented by the following general formula (1):Ru--I.sub.2 --(R.sup.1 -BINAP) (1)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by the following general formula (2): ##STR1## wherein R.sup.1 represents an aryl group which may have a substituent selected from the group consisting of a C.sub.1-4 lower alkyl group, a C.sub.1-4 lower alkoxy group, a C.sub.1-4 lower alkylamino group, and a halogen atom or a C.sub.3-8 cycloalkyl group.
摘要翻译：本发明提供一种催化活性高的催化剂，能够以不对称产率进行不对称反应，得到光学纯度高的反应产物。本发明还提供了在上述催化剂存在下，在短时间内以高收率制备具有高光学纯度的光学纯度高的光学活性4-甲基-2-氧杂环丁酮的方法。提供了由以下通式（1）表示的新型钌 - 碘 - 光学活性膦配合物：Ru-I2-（R1-BINAP）（1）其中R1-BINAP表示由以下通式表示的光学活性叔膦式（2）：其中R1表示可以具有选自C 1-4低级烷基，C 1-4低级烷氧基，C 1-4低级烷基氨基和卤素原子的取代基的芳基或C 3-8环烷基。

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