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    Process for preparing optically active 4-hydroxy-2-pyrrolidone
    52.
    发明授权
    Process for preparing optically active 4-hydroxy-2-pyrrolidone 失效
    制备光学活性4-羟基-2-吡咯烷酮的方法

    公开(公告)号：US5837877A

    公开(公告)日：1998-11-17

    申请号：US790931

    申请日：1997-01-29

    申请人： Shigeru Mitsuhashi ,  Hidenori Kumobayashi

    发明人： Shigeru Mitsuhashi ,  Hidenori Kumobayashi

    IPC分类号： B01J31/24 ,  C07B53/00 ,  C07B61/00 ,  C07D207/26 ,  C07D207/273

    CPC分类号： C07D207/273

    摘要： A process for preparing optically active 4-hydroxy-2-pyrrolidone comprising asymmetrically hydrogenating an N-substituted-4-amino-3-oxobutanoic ester represented by formula (I): ##STR1## wherein R.sup.1 represents a benzyloxycarbonyl group, the benzene ring of which may be substituted; and R.sup.2 represents a lower alkyl group having 1 to 4 carbon atoms, in the presence of a ruthenium-optically active phosphine complex as a catalyst to obtain an optically active N-substituted-4-amino-3-hydroxybutanoic ester, deblocking, and cyclizing the ester. A series of the reactions can be carried out in one pot. Optically active 4-hydroxy-2-pyrrolidone is obtained in high yield with high optical purity, and is useful in the synthesis of carbapenem antibiotics

    摘要翻译： 一种制备光学活性的4-羟基-2-吡咯烷酮的方法，包括用式（I）表示的N-取代-4-氨基-3-氧代丁酸酯不对称氢化：其中R1代表苄氧基羰基， 苯环可以被取代; 在钌光学活性膦配合物作为催化剂的存在下，R 2表示具有1〜4个碳原子的低级烷基，得到光学活性的N-取代-4-氨基-3-羟基丁酸酯，去封闭和环化 酯。 一系列反应可以在一锅中进行。 以高光学纯度获得光学活性的4-羟基-2-吡咯烷酮，可用于合成碳青霉烯类抗生素

    Phosphine compound, complex containing the phosphine compound as ligand, process for producing optically active aldehyde using the phosphine compound or the complex, and 4-[(R)-1'-formylethyl]azetidin-2-one derivatives
    53.
    发明授权
    Phosphine compound, complex containing the phosphine compound as ligand, process for producing optically active aldehyde using the phosphine compound or the complex, and 4-[(R)-1'-formylethyl]azetidin-2-one derivatives 失效
    膦化合物，含膦化合物作为配体的络合物，使用膦化合物或络合物制备旋光醛的方法，以及4 - [（R）-1'-甲酰基乙基]氮杂环丁-2-酮衍生物

    公开(公告)号：US5530150A

    公开(公告)日：1996-06-25

    申请号：US323492

    申请日：1994-10-12

    申请人： Hidemasa Takaya ,  Nozomu Sakai ,  Kyoko Tamao ,  Satoshi Mano ,  Hidenori Kumobayashi ,  Tetsuo Tomita ,  Takao Saito ,  Kazuhiko Matsumura ,  Yasushi Kato ,  Noboru Sayo

    发明人： Hidemasa Takaya ,  Nozomu Sakai ,  Kyoko Tamao ,  Satoshi Mano ,  Hidenori Kumobayashi ,  Tetsuo Tomita ,  Takao Saito ,  Kazuhiko Matsumura ,  Yasushi Kato ,  Noboru Sayo

    IPC分类号： C07F9/02 ,  C07F15/00

    CPC分类号： C07F9/02 ,  C07F15/00

    摘要： A phosphine compound represented by one of the formulas: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R.sup.3 and R.sup.4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R.sup.6 and R.sup.6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.5, R.sup.5', R.sup.11 and R.sup.11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R.sup.5 and R.sup.6 or a pair of R.sup.5' and R.sup.6' may form a ring; R.sup.7 and R.sup.8, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a lower alkyl group, a halogen atom or a lower alkoxy group; and R.sup.9 and R.sup.10, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a lower alkyl group, a lower alkoxy group or a halogen atom; or R.sup.9 and R.sup.10 may be taken together to form a divalent hydrocarbon group.

    摘要翻译： 由下式之一表示的膦化合物：其中R 1和R 2可以相同或不同，各自表示苯基或苯基（III），其中R 1和R 2可以相同或不同， 被卤素原子或低级烷基取代或一起形成二价烃基; 和可以相同或不同的R 3和R 4各自表示低级烷基，苯基或被卤素原子，低级烷基或低级烷氧基取代的苯基或一起形成二价烃基 并且其中可以相同或不同的R6和R6'各自表示氢原子，低级烷基或低级烷氧基; R5，R5'，R11和R11'可以相同或不同，分别表示氢原子，低级烷基，低级烷氧基或卤素原子; 或一对R 5和R 6或一对R 5'和R 6'可以形成环; R 7和R 8可以相同或不同，表示苯基或被低级烷基，卤原子或低级烷氧基取代的苯基; 和R 9和R 10可以相同或不同，各自表示苯基或被低级烷基，低级烷氧基或卤素原子取代的苯基; 或者R 9和R 10可以一起形成二价烃基。

    Water-soluble alkali metal sulfonate-substituted binaphthylphosphine transition metal complex and enantioselective hydrogenation method using it
    54.
    发明授权
    Water-soluble alkali metal sulfonate-substituted binaphthylphosphine transition metal complex and enantioselective hydrogenation method using it 失效
    水溶性碱金属磺酸盐取代的二萘基膦过渡金属络合物及其对映选择性氢化法

    公开(公告)号：US5324861A

    公开(公告)日：1994-06-28

    申请号：US116583

    申请日：1993-09-07

    申请人： Takerou Ishizaki ,  Hidenori Kumobayashi

    发明人： Takerou Ishizaki ,  Hidenori Kumobayashi

    IPC分类号： B01J31/22 ,  B01J31/24 ,  C07B61/00 ,  C07C211/27 ,  C07C213/00 ,  C07C215/20 ,  C07C215/28 ,  C07F9/50 ,  C07F15/00 ,  C07C45/00

    CPC分类号： C07F15/008 ,  B01J31/2291 ,  B01J31/2295 ,  B01J31/2452 ,  C07F15/0013 ,  C07F15/004 ,  C07F15/0053 ,  C07F15/0066 ,  B01J2231/643 ,  B01J2231/645 ,  B01J2531/0266 ,  B01J2531/821 ,  B01J2531/822 ,  B01J2531/824 ,  B01J2531/827 ,  B01J2531/96

    摘要： An alkali metal sulfonate-substituted binaphthyl-phosphine transition metal complex is disclosed, which is represented by formula (I)[M(X).sub.n (Q)(SO.sub.3 A--BINAP)]Y (I)wherein M represents a transition metal atom; SO.sub.3 A--BINAP represents a tertiary phosphine represented by formula (II) ##STR1## in which A represents an alkali metal atom; X represents a chlorine atom, a bromine atom, or an iodine atom;when n is 1, M represents ruthenium, Q represents benzene or p-cymene, and Y represents a chlorine atom, a bromine atom, or an iodine atom;when n is 0 and M is iridium or rhodium, Q represents 1,5-cyclo-octadiene or norbornadiene, and Y represents ClO.sub.4, PF.sub.6 or BF.sub.4 ; and when n is 0 and M is palladium, Q represents .pi.-allyl, and Y represents ClO.sub.4, PF.sub.6, or BF.sub.4. A method of enantioselectively hydrogenating an olefin, a ketone, or an imine, which comprises carrying out the enantioselective hydrogenation using as a catalyst the alkali metal sulfonate-substituted binaphthylphosphine transition metal complex represented by formula (I) is also disclosed.

    摘要翻译： 公开了由式（I）[M（X）n（Q）（SO 3 A-BINAP）] Y（I）表示的碱金属磺酸盐取代的联萘膦过渡金属络合物，其中M表示过渡金属原子; SO 3 -A-BINAP表示由式（II）表示的叔膦，其中A表示碱金属原子; X表示氯原子，溴原子或碘原子; 当n为1时，M表示钌，Q表示苯或对 - 异丙基苯，Y表示氯原子，溴原子或碘原子; 当n为0且M为铱或铑时，Q为1,5-环辛二烯或降冰片二烯，Y为ClO 4，PF 6或BF 4; 当n为0且M为钯时，Q为吡咯烷基，Y为ClO4，PF6或BF4。 还公开了一种使烯烃，酮或亚胺对映选择性氢化的方法，其包括使用由式（I）表示的碱金属磺酸盐取代的二萘基膦过渡金属络合物作为催化剂进行对映选择性氢化。

    Iridium-optically active phosphine complex and process for producing optically active alcohols using the same
    57.
    发明授权
    Iridium-optically active phosphine complex and process for producing optically active alcohols using the same 失效
    铱 - 光学活性膦配合物和使用其制备光学活性醇的方法

    公开(公告)号：US5210332A

    公开(公告)日：1993-05-11

    申请号：US856403

    申请日：1992-03-20

    申请人： Takanao Taketomi ,  Susumu Akutagawa ,  Hidenori Kumobayashi ,  Hidemasa Takaya ,  Kazushi Mashima

    发明人： Takanao Taketomi ,  Susumu Akutagawa ,  Hidenori Kumobayashi ,  Hidemasa Takaya ,  Kazushi Mashima

    IPC分类号： C07F15/00

    CPC分类号： C07F15/004

    摘要： An iridium-optically active phosphine complex represented by formula (I):[H.sub.2 Ir(L.sup.1)(L.sup.2)]Y (I)wherein L.sup.1 represents an optically active phosphine compound represented by formula (II): ##STR1## wherein Ar represents a phenyl group or a p- and/or m-lower alkyl-substituted phenyl group, or formula (III): ##STR2## L.sup.2 represents a tertiary phosphine compound represented by formula (IV): ##STR3## wherein Z represents a lower alkoxy group or a di-lower alkylamino group; and A represents an integer of from 1 to 3; Y represents BF.sub.4, PF.sub.6, ClO.sub.4, or BPh.sub.4, wherein Ph represents a phenyl group,and a process for producing an optically active alcohol using the above complex as an enantioselective catalyst are disclosed. The complex exhibits excellent catalytic activity to give high enantioselective yields in enantioselective synthesis, particularly enantioselective hydrogenation.

    摘要翻译： 由式（I）表示的铱光学活性膦配合物：[H2Ir（L1）（L2）] Y（I）其中L1表示由式（II）表示的光学活性膦化合物：其中Ar （III）表示式（IV）表示的叔膦化合物：（IV）表示的叔膦化合物：其中， ）其中Z表示低级烷氧基或二低级烷基氨基; A表示1〜3的整数， Y表示BF4，PF6，ClO4或BPh4，其中Ph表示苯基，并且公开了使用上述络合物作为对映选择性催化剂制备光学活性醇的方法。 复合物显示出优异的催化活性，以在对映选择性合成，特别是对映选择性氢化中提供高对映选择性的产率。

    Process for production of optically active 2-(tetrahydropyran-2-yloxy)-1-propanol
    58.
    发明授权
    Process for production of optically active 2-(tetrahydropyran-2-yloxy)-1-propanol 失效
    生产光学活性2-（四氢吡喃-2-基）-1-丙醇的方法

    公开(公告)号：US5128489A

    公开(公告)日：1992-07-07

    申请号：US592752

    申请日：1990-10-04

    申请人： Hidenori Kumobayashi ,  Akio Tachikawa ,  Yoshiki Okeda ,  Toshihiro Fujiwara

    发明人： Hidenori Kumobayashi ,  Akio Tachikawa ,  Yoshiki Okeda ,  Toshihiro Fujiwara

    IPC分类号： C07D309/12 ,  C07D498/06

    CPC分类号： C07D309/12

    摘要： A process for production of an optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I): ##STR1## is disclosed, which comprises reacting an optically active isomer of a 1-acyloxy-2-propanol represented by formula (II): ##STR2## wherein R is a substituted or unsubstituted aryl group, with 3,4-dihydro-2H-pyran to obtain an optically active isomer of a 1-acyloxy-2-(tetrahydropyran-2-yloxy)propane represented by formula (III): ##STR3## wherein R is as defined above, and hydrolyzing the compound (III) to eliminate the acyl group. The optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I) is an intermediate for synthesis of pyridobenzoxazine derivatives useful as a synthetic antibacterial agent, particularly an optically active isomer of ofloxacin.

    Process for producing optically active carboxylic acid
    59.
    发明授权
    Process for producing optically active carboxylic acid 失效
    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.