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    BIDENTATE CHIRAL LIGANDS FOR USE IN CATALYTIC ASYMMETRIC ADDITION REACTIONS
    2.
    发明申请
    BIDENTATE CHIRAL LIGANDS FOR USE IN CATALYTIC ASYMMETRIC ADDITION REACTIONS 有权
    用于催化不对称添加反应的双歧杆菌配体

    公开(公告)号：US20110118482A1

    公开(公告)日：2011-05-19

    申请号：US12734696

    申请日：2008-11-14

    申请人： Benoît Pugin ,  Matthias Lotz ,  Heidi Landert ,  Adrian Wyss ,  Raphael Aardoom ,  Bjõrn Gschwend ,  Andreas Pfaltz ,  Felix Spindler

    发明人： Benoît Pugin ,  Matthias Lotz ,  Heidi Landert ,  Adrian Wyss ,  Raphael Aardoom ,  Bjõrn Gschwend ,  Andreas Pfaltz ,  Felix Spindler

    IPC分类号： C07F9/6553 ,  C07F15/00 ,  C07F17/02 ,  C07F9/28 ,  C07F9/655 ,  C07C67/00 ,  C07C227/16

    CPC分类号： C07F13/005 ,  B01J31/1875 ,  B01J31/2291 ,  B01J31/2495 ,  B01J2231/643 ,  B01J2231/645 ,  B01J2531/0238 ,  B01J2531/822 ,  B01J2531/827 ,  C07B53/00 ,  C07B2200/07 ,  C07C67/303 ,  C07C67/31 ,  C07C231/12 ,  C07C231/18 ,  C07F9/46 ,  C07F9/5004 ,  C07F9/5018 ,  C07F9/5022 ,  C07F9/5027 ,  C07F9/65515 ,  C07F9/65517 ,  C07F9/65522 ,  C07F9/655354 ,  C07F17/02 ,  C07C69/34 ,  C07C69/732 ,  C07C69/675 ,  C07C233/47

    摘要： Compounds of the formula (I), in the form of mixtures comprising predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1 (I) in which Z1 is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals, or Z1 is the —P*R0R1 group; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group Z1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*R0R1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; R0 is methyl or hydroxyl, and R0 is methyl when Z1 is the —P*R0R1 group; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon or heterohydrocarbon radical which has 3 to 12 ring atoms and 1 to 4 rings and which has a stereogenic carbon atom at least in the a position to the P—C bond; Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.

    摘要翻译： 主要为一种非对映体或纯非对映体形式的混合物形式的式（I）化合物，其中Z 1为C键，仲膦基-P（R）的Z1-QP * R0R1（I） 2; 其中R各自独立地为烃基或杂烃基，或Z1为-P * R0R1基团; Q是二价，非手性，芳族碱基骨架，二价，非手性二茂铁碱骨架，任选取代的二价环烷烃或杂环烷骨架，或C1-C4-亚烷基骨架，其中，基骨架中的次膦基Z1直接键合 或在环状基团骨架的情况下直接与碳原子或C 1 -C 4 - 亚烷基直接键合，并且其中的基础骨架中，P手性基团-P * R0R1直接键合到碳上 或者在环状基骨架的情况下，直接连接到碳原子上，或者通过C1-C4-亚烷基与碳原子连接，使得磷原子通过1至7个任选被杂原子中断的碳链原子连接 由O，S，N，Fe或Si组成; P *是手性磷原子; R 0是甲基或羟基，当Z 1是-P * R 0 R 1基团时，R 0是甲基; 并且R 1是C-键合的光学富集或光学纯的手性，单或多环，非芳族烃或杂烃基，其具有3至12个环原子和1至4个环，并且其具有立体碳原子至少在 P-C键; 这些配体的金属络合物是用于不对称加成反应的均相催化剂，特别是氢化。

    Bidentate secondary phosphine oxide chiral ligands for use in asymmetric addition reactions
    3.
    发明授权
    Bidentate secondary phosphine oxide chiral ligands for use in asymmetric addition reactions 失效
    用于不对称加成反应的二齿次膦氧化物手性配体

    公开(公告)号：US08415488B2

    公开(公告)日：2013-04-09

    申请号：US12734726

    申请日：2008-11-14

    申请人： Benoît Pugin ,  Heidi Landert ,  Björn Gschwend ,  Andreas Pfaltz ,  Felix Spindler

    发明人： Benoît Pugin ,  Heidi Landert ,  Björn Gschwend ,  Andreas Pfaltz ,  Felix Spindler

    IPC分类号： C07D333/62

    CPC分类号： C07F9/65517 ,  B01J31/2495 ,  B01J2231/643 ,  B01J2231/645 ,  B01J2531/822 ,  B01J2531/827 ,  C07B53/00 ,  C07B2200/07 ,  C07C67/303 ,  C07C67/31 ,  C07C213/02 ,  C07C231/12 ,  C07C231/18 ,  C07F9/46 ,  C07F9/5018 ,  C07F9/5022 ,  C07F9/655354 ,  C07C69/34 ,  C07C69/732 ,  C07C69/675 ,  C07C217/08 ,  C07C233/47

    摘要： Compounds of the formula I, in the form of mixtures comprising predominantly one enantiomer or in the form of pure enantiomers, secondary phosphine-Q-P*(═O)HR1 (I) in which secondary phosphine is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*(O)HR1 is bonded to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; and R1 is a hydrocarbon radical, a C-bonded heterohydrocarbon radical or a ferrocenyl radical, with the proviso that R1 is an achiral ferrocenyl radical when Q is an achiral ferrocenyl base skeleton. Metal complexes of these ligands in a molar ratio of ligand to metal of about 1.3:1 to 0.9:1 are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.

    摘要翻译： 主要以一种对映体或纯对映异构体形式的混合物形式的式I化合物，其中次膦是C键，仲膦基的仲膦-PQ *（= O）HR1（I） P（R）2; 其中R各自独立地为烃基或杂烃基; Q是二价，非手性，芳族碱基骨架，二价，非手性二茂铁碱骨架，任选取代的二价环烷烃或杂环烷骨架，或C 1 -C 4亚烷基骨架，其中碱基骨架的仲膦基直接键合到 碳原子，或者在环状基骨架的情况下，直接与碳原子或C 1 -C 4 - 亚烷基直接键合，并且其中的基础骨架将P手性基团-P *（O）HR1键合到 碳原子，使得磷原子通过1至7个碳链连接，任选被来自O，S，N，Fe或Si基团的杂原子中断; P *是手性磷原子; 并且R 1是烃基，C键合的杂烃基或二茂铁基，条件是当Q是非手性二茂铁基时，R 1是非手性二茂铁基。 配体与金属的摩尔比约为1.3:1至0.9:1的这些配体的金属络合物是用于不对称加成反应，特别是氢化的均相催化剂。

    BIDENTATE SECONDARY PHOSPHINE OXIDE CHIRAL LIGANDS FOR USE IN ASYMMETRIC ADDITION REACTIONS
    4.
    发明申请
    BIDENTATE SECONDARY PHOSPHINE OXIDE CHIRAL LIGANDS FOR USE IN ASYMMETRIC ADDITION REACTIONS 失效
    用于非对称添加反应的二次磷酸二氢氧化锡配体

    公开(公告)号：US20110098485A1

    公开(公告)日：2011-04-28

    申请号：US12734726

    申请日：2008-11-14

    申请人： Benoît Pugin ,  Heidi Landert ,  Björn Gschwend ,  Andreas Pfaltz ,  Felix Spindler

    发明人： Benoît Pugin ,  Heidi Landert ,  Björn Gschwend ,  Andreas Pfaltz ,  Felix Spindler

    IPC分类号： C07D333/50 ,  C07F9/28 ,  C07F15/00 ,  C07C41/00 ,  C07C205/00 ,  C07D295/027 ,  C07C315/00

    CPC分类号： C07F9/65517 ,  B01J31/2495 ,  B01J2231/643 ,  B01J2231/645 ,  B01J2531/822 ,  B01J2531/827 ,  C07B53/00 ,  C07B2200/07 ,  C07C67/303 ,  C07C67/31 ,  C07C213/02 ,  C07C231/12 ,  C07C231/18 ,  C07F9/46 ,  C07F9/5018 ,  C07F9/5022 ,  C07F9/655354 ,  C07C69/34 ,  C07C69/732 ,  C07C69/675 ,  C07C217/08 ,  C07C233/47

    摘要： Compounds of the formula I, in the form of mixtures comprising predominantly one enantiomer or in the form of pure enantiomers, secondary phosphine-Q-P*(═O)HR1 (I) in which secondary phosphine is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*(O)HR1 is bonded to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally interrupted by heteroatoms from the group of O, S, N, Fe or Si; P* is a chiral phosphorus atom; and R1 is a hydrocarbon radical, a C-bonded heterohydrocarbon radical or a ferrocenyl radical, with the proviso that R1 is an achiral ferrocenyl radical when Q is an achiral ferrocenyl base skeleton. Metal complexes of these ligands in a molar ratio of ligand to metal of about 1.3:1 to 0.9:1 are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.

    摘要翻译： 主要以一种对映体或纯对映异构体形式的混合物形式的式I化合物，其中次膦是C键，仲膦基的仲膦-PQ *（= O）HR1（I） P（R）2; 其中R各自独立地为烃基或杂烃基; Q是二价，非手性，芳族碱基骨架，二价，非手性二茂铁碱骨架，任选取代的二价环烷烃或杂环烷骨架，或C 1 -C 4亚烷基骨架，其中碱基骨架的仲膦基直接键合到 碳原子，或者在环状基骨架的情况下，直接与碳原子或C 1 -C 4 - 亚烷基直接键合，并且其中的基础骨架将P手性基团-P *（O）HR1键合到 碳原子，使得磷原子通过1至7个碳链连接，任选被来自O，S，N，Fe或Si基团的杂原子中断; P *是手性磷原子; 并且R 1是烃基，C键合的杂烃基或二茂铁基，条件是当Q是非手性二茂铁基时，R 1是非手性二茂铁基。 配体与金属的摩尔比约为1.3:1至0.9:1的这些配体的金属络合物是用于不对称加成反应，特别是氢化的均相催化剂。

    Method for producing orthometalated and orthosubstituted metallocenes
    5.
    发明授权
    Method for producing orthometalated and orthosubstituted metallocenes 失效
    生产原位金属和原位取代金属茂的方法

    公开(公告)号：US07435840B2

    公开(公告)日：2008-10-14

    申请号：US10582404

    申请日：2004-12-10

    申请人： Andreas Pfaltz ,  Matthias Lotz ,  Marc Schönleber ,  Benoît Pugin ,  Martin Kesselgruber ,  Marc Thommen

    发明人： Andreas Pfaltz ,  Matthias Lotz ,  Marc Schönleber ,  Benoît Pugin ,  Martin Kesselgruber ,  Marc Thommen

    IPC分类号： C07F15/00 ,  B01J31/00

    CPC分类号： C07F9/65848 ,  C07F17/02

    摘要： The invention relates to compounds having a structural element of formula (I) in an aromatic hydrocarbon ring, wherein: M represents —Li, —MgX3, (C1-C18-Alkyl)3Sn—, —ZnX3 or —B(O—C1-C4-Alkyl)2; X1 and X2, independent of one another, represent O or N, and C-bound hydrocarbon radicals or heterohydrocarbon radicals are bound to the free bonds of the O and N atoms; group —C═C—, together with C atoms, forms a hydrocarbon aromatic compound and represents X3 Cl, Br or I. The inventive compounds are easily obtained by directly substituting the hydrogen in the ortho position to the P atom with metalation reagents. The metal atoms can then be substituted by a reactive electrophilic compound. The group —P(X1—)(X2—) - - - -(BH3)0,1 can then be converted into a secondary phosphine group. The inventive method enables the production of monophosphines and diphosphines even on a large scale, which are valuable ligands for metal complexes serving as catalysts for, e.g. enantioselective hydrogenations.

    摘要翻译： 本发明涉及在芳族烃环中具有式（I）结构元件的化合物，其中：M表示-Li，-MgX 3，（C 1 -C 3） 烷基）3-Sn-，-ZnX 3或-B（OC 1 -C 3） 4 - 烷基）2 然后可以转化成次膦基。 本发明的方法甚至可以大量生产单膦和二膦，这是用作金属络合物的有价值的配体，用作催化剂。 对映选择性氢化。

    Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation
    6.
    发明授权
    Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation 有权
    用于非对称加成反应的过渡金属催化剂中的手性配体，特别是氢化

    公开(公告)号：US08008529B2

    公开(公告)日：2011-08-30

    申请号：US12227574

    申请日：2007-05-23

    申请人： Andreas Pfaltz ,  Yann Ribourdouille ,  Xiangdong Feng ,  Balamurugan Ramalingam ,  Benoît Pugin ,  Felix Spindler

    发明人： Andreas Pfaltz ,  Yann Ribourdouille ,  Xiangdong Feng ,  Balamurugan Ramalingam ,  Benoît Pugin ,  Felix Spindler

    IPC分类号： C07F15/02 ,  C07F9/53 ,  C07C69/34 ,  B01J31/18

    CPC分类号： C07F9/5022 ,  B01J31/1875 ,  B01J31/2495 ,  B01J2231/643 ,  B01J2231/645 ,  B01J2531/821 ,  B01J2531/822 ,  B01J2531/827 ,  C07B2200/07 ,  C07C51/36 ,  C07C67/303 ,  C07C213/02 ,  C07C231/12 ,  C07F15/008 ,  C07F17/02 ,  C07C57/30 ,  C07C69/675 ,  C07C69/732 ,  C07C69/34 ,  C07C217/08 ,  C07C233/47

    摘要： Ligands of the formula (I) secondary phosphine-Q-P(═O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the —P*(═O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre when Q is a ferrocenyl radical without a planar chiral centre. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.

    摘要翻译： 式（I）以非对映异构体或纯非对映异构体混合物形式的仲膦-Q-P（= O）HR1（I）的配体，其中次膦是具有烃基或杂烃基作为取代基的次膦基; Q是具有轴向手性中心的二价双芳基或双杂芳基，其中两个磷原子与双芳基或双杂芳基桥键的邻位键合，或Q是具有平面手性中心或不具有平面手性的二价二茂铁基 中心，仲膦的磷原子直接或通过C1-C4-碳键连接到环戊二烯基环上，-P *（= O）HR 1基团在邻位上的相同的环戊二烯基环上键合到 键合的次膦或在另一个环戊二烯基环上; P *是手性磷原子，R1是烃基，杂烃基或二茂铁基，其中当Q是没有平面手性中心的二茂铁基时，R 1是具有平面手性中心的二茂铁基。 这些配体的金属络合物是用于不对称加成反应的均相催化剂，特别是氢化。

    CHIRAL LIGANDS
    7.
    发明申请
    CHIRAL LIGANDS 审中-公开

    公开(公告)号：US20110275826A1

    公开(公告)日：2011-11-10

    申请号：US13141379

    申请日：2009-12-22

    申请人： Andreas Pfaltz ,  Marcus Georg Schrems ,  Benoît Pugin

    发明人： Andreas Pfaltz ,  Marcus Georg Schrems ,  Benoît Pugin

    IPC分类号： C07F15/00 ,  C07F7/18 ,  C07F9/653

    CPC分类号： C07F9/653 ,  C07B53/00 ,  C07F15/0033

    摘要： Chiral compounds of the formula (1), which are optically pure or highly optically enriched in which R0 is C1-C12-alkyl which is unsubstituted or substituted by 1 to 2 C1-C4-alkoxy; cyclo-pentyl or cyclohexyl, which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl or C1-C4-alkoxy; or benzyl, phenyl or naphtyl which is unsubstituted or substituted by 1 to 3 C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl or C1-C4-fluoroalkoxy, F or Cl, or R0 is —CR5R6OH or —CR5R6OSi(C1-C8-alkyl)3 wherein R5 and R6 are independently selected from the group consisting of H, unsubstituted C1-C12 alkyl, substituted C1-C12 alkyl, unsubstituted C4-C8 cyclo alkyl, substituted C4-C8 cyclo alkyl, unsubstituted aryl, substituted aryl or wherein R5 and R6 can form an unsubstituted 5-6 membered aliphatic carbocycle or a substituted 5-6 membered aliphatic carbocycle, each of R1 and R′1 independently is hydrogen or has the meaning of R0 whereby R1, R′1 and R0 can be same or different, R2 and R3 are independently a C-bonded hydrocarbon radical or a heterohydrocarbon radical, and each of both R4 is C1-C6-alkyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, methylbenzyl or benzyl, or both R4 together form an aliphatic C4-C6 carbocycle. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reaction, particularly hydrogenations.

    摘要翻译： 式（1）的手性化合物，其是光学纯的或高度光学富集的，其中R 0是未被取代或被1至2个C 1 -C 4 - 烷氧基取代的C 1 -C 12 - 烷基; 环戊基或环己基，其是未取代的或被1至3个C 1 -C 4 - 烷基或C 1 -C 4 - 烷氧基取代; 或未被取代或被1至3个C 1 -C 4 - 烷基，C 1 -C 4 - 烷氧基，C 1 -C 4 - 氟代烷基或C 1 -C 4 - 氟烷氧基，F或Cl或R 10表示的苄基，苯基或萘基是-CR 5 R 6 OH或 - CR5R6OSi（C1-C8-烷基）3，其中R5和R6独立地选自H，未取代的C1-C12烷基，取代的C1-C12烷基，未取代的C4-C8环烷基，取代的C4-C8环烷基，未取代的 芳基，取代的芳基或其中R5和R6可以形成未取代的5-6元脂族碳环或取代的5-6元脂族碳环，R 1和R'1各自独立地是氢或具有R 0的含义，其中R 1，R' 1和R 0可以相同或不同，R2和R3独立地是C键合的烃基或杂烃基，并且R 2各自为C 1 -C 6 - 烷基，环戊基，环己基，苯基，甲基苯基，甲基苄基或苄基，或 R4一起形成脂族C 4 -C 6碳环。 这些配体的金属络合物是用于不对称加成反应，特别是氢化的均相催化剂。

    Ferrocenyl-1,2-diphosphines, the production thereof and their use
    10.
    发明授权
    Ferrocenyl-1,2-diphosphines, the production thereof and their use 失效
    二茂铁基-1,2-二膦，其生产及其用途

    公开(公告)号：US07375241B2

    公开(公告)日：2008-05-20

    申请号：US10582406

    申请日：2004-12-10

    申请人： Matthias Lotz ,  Martin Kesselgruber ,  Marc Thommen ,  Benoît Pugin

    发明人： Matthias Lotz ,  Martin Kesselgruber ,  Marc Thommen ,  Benoît Pugin

    IPC分类号： C07F5/02 ,  C07F15/00 ,  C07C229/00 ,  C07C69/34

    CPC分类号： C07C233/51 ,  C07B2200/07 ,  C07C67/303 ,  C07C233/48 ,  C07C2601/14 ,  C07F17/02 ,  C07C69/34

    摘要： The invention relates to compounds of formula (I) provided in the form of racemic compounds, mixtures of diastereomers or essentially pure diastereomers, wherein R1 represents a hydrogen atom or C1-C4-alkyl, and at least one secondary phosphine depicts an unsubstituted or substituted cyclic phosphine group, or phosphonium salts thereof having one or two monovalent anions or a divalent anion. The compounds of formula (I) can be obtained by means of a novel method and are valuable ligands for catalytically active metal complexes in asymmetrical synthesis

    摘要翻译： 本发明涉及以消旋化合物的形式提供的式（I）化合物，非对映异构体或基本上纯的非对映异构体的混合物，其中R 1表示氢原子或C 1〜 -C 4 - 亚烷基，至少一个仲膦表示未取代或取代的环膦基，或其具有一个或两个单价阴离子或二价阴离子的鏻盐。 式（I）化合物可以通过新的方法获得，并且是不对称合成中催化活性金属络合物的有价值的配体