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    Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation
    1.
    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 Used in Transition Metal Catysts for Asymmetric Addition Reactions Especially Hydrogenation
    2.
    发明申请
    Chiral Ligands Used in Transition Metal Catysts 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：US20090171114A1

    公开(公告)日：2009-07-02

    申请号：US12227574

    申请日：2007-05-23

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

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

    IPC分类号： C07C69/34 ,  C07F15/02 ,  C07F9/53 ,  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仲膦基; 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基团在邻位相邻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。

    BIDENTATE CHIRAL LIGANDS FOR USE IN CATALYTIC ASYMMETRIC ADDITION REACTIONS
    4.
    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
    5.
    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
    6.
    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。

    Ferrocenediphosphines
    9.
    发明授权
    Ferrocenediphosphines 有权
    二茂铁

    公开(公告)号：US08106227B2

    公开(公告)日：2012-01-31

    申请号：US12226213

    申请日：2007-04-11

    申请人： Weiping Chen ,  Felix Spindler ,  Benoît Pugin

    发明人： Weiping Chen ,  Felix Spindler ,  Benoît Pugin

    IPC分类号： C07F15/02

    CPC分类号： C07F17/02 ,  C07B53/00 ,  C07F9/52

    摘要： Compounds of the formula I in the form of enantiomerically pure diastereomers or a mixture of diastereomers, (I), where the radicals R1 are identical or different and are each C1-C4-alkyl; m is 0 or an integer from 1 to 3; n is 0 or an integer from 1 to 4; R2 is a hydrocarbon radical or a C-bonded heterohydrocarbon radical; Cp is unsubstituted or C1-C4-alkyl-substituted cyclopentadienyl; Y is a C-bonded chiral group which directs metals of metallation reagents into the ortho position; and Phos is a P-bonded P(III) substituent. The compounds are chiral ligands for complexes of transition metals which are used as homogeneous catalysts in asymmetric syntheses.

    摘要翻译： 式I化合物为对映体纯的非对映体形式或非对映异构体（I）的混合物，其中基团R 1相同或不同并且各自为C 1 -C 4 - 烷基; m为0或1〜3的整数; n为0或1至4的整数; R2是烃基或C键合的杂烃基; Cp是未取代的或C 1 -C 4烷基取代的环戊二烯基; Y是将金属化试剂的金属引导到邻位的C-键合手性基团; Phos是P键合的P（III）取代基。 这些化合物是用于不对称合成中的均相催化剂的过渡金属络合物的手性配体。

    Diphosphine ligands
    10.
    发明申请
    Diphosphine ligands 审中-公开
    二膦配体

    公开(公告)号：US20100029967A1

    公开(公告)日：2010-02-04

    申请号：US12308941

    申请日：2007-06-29

    申请人： Benoit Pugin ,  Xiangdong Feng ,  Felix Spindler

    发明人： Benoit Pugin ,  Xiangdong Feng ,  Felix Spindler

    IPC分类号： C07F15/00

    CPC分类号： C07F17/00 ,  B01J31/2295 ,  B01J31/2409 ,  B01J31/2428 ,  B01J2231/643 ,  B01J2231/645 ,  B01J2531/16 ,  B01J2531/17 ,  B01J2531/18 ,  B01J2531/821 ,  B01J2531/822 ,  B01J2531/824 ,  B01J2531/825 ,  B01J2531/827 ,  B01J2531/842 ,  B01J2531/845 ,  B01J2531/847 ,  C07B53/00 ,  C07F17/02

    摘要： Compounds of the formulae I and Ia in the form of mixtures of diastereomers or pure diastereomers, (I), (Ia), where R1 is a hydrogen atom or C1-C4-alkyl and R′1 is C1-C4-alkyl; X1 and X2 are each, independently of one another, a sec-phosphino group; T is C6-C20-arylene or C4-C18-heteroarylene having heteroatoms selected from the group consisting of O, S, —N═ and N(C1-C4-alkyl); v is 0 or an integer from 1 to 4; X1 is bound in the ortho position relative to the T-C* bond; Q is vinyl, methyl, ethyl, —CH2—OR, —CH2—N(C1-C4-alkyl)2 or a C- or S-bonded chiral group which directs metals of metallation reagents into the ortho position; R is hydrogen, a silyl radical or an aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic hydrocarbon radical which has from 1 to 18 carbon atoms and is unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, F or CF3; are ligands for metal complexes as homogeneous catalyst in asymmetric syntheses.

    摘要翻译： 式（I），（Ia），其中R 1是氢原子或C 1 -C 4 - 烷基和R 11是C 1 -C 4 - 烷基的非对映异构体或纯非对映体混合物形式的式I和Ia化合物; X1和X2各自独立地为仲膦基; T是具有选自O，S，-N-和N（C 1 -C 4 - 烷基）的杂原子的C 6 -C 20亚芳基或C 4 -C 18亚杂芳基; v为0或1至4的整数; X1相对于T-C *键的邻位结合; Q是乙烯基，甲基，乙基，-CH 2 -OR，-CH 2 -N（C 1 -C 4烷基）2或C-或S-键合的手性基团，其将金属化试剂的金属引导到邻位; R是氢，具有1至18个碳原子且未被取代或被C 1 -C 4 - 烷基，C 1 -C 4 - 烷氧基，F或CF 3取代的甲硅烷基或脂族，脂环族，芳族或芳族 - 脂族烃基; 是不对称合成中金属络合物作为均相催化剂的配体。