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    Method for producing chiral mercapto amino acids
    1.
    发明申请
    Method for producing chiral mercapto amino acids 审中-公开

    公开(公告)号：US20070112216A1

    公开(公告)日：2007-05-17

    申请号：US10581790

    申请日：2004-11-15

    申请人： Martina Kotthaus ,  Herbert Mayrhofer ,  Christian Rogl ,  Sylvia Krich ,  Michael Simetzberger

    发明人： Martina Kotthaus ,  Herbert Mayrhofer ,  Christian Rogl ,  Sylvia Krich ,  Michael Simetzberger

    IPC分类号： C07C323/29

    CPC分类号： C07C319/06 ,  C07B2200/07 ,  C07C323/58

    摘要： The invention relates to a method for producing chiral mercapto amino acids of formula (I) wherein R1, R2 and R3 can represent hydrogen, C6-C12 aryl, C1-C6-alkyl-C6-C12-aryl, C6-C12-aryl-C1-C6-alkyl, C1-C18-alkyl or C2-C18-alkenyl, R2 and R3 forming a saturated or unsaturated ring. According to said method, a) an oxo compound of formula (II), wherein X represents a leaving group, is reacted in the presence of ammonia or ammonium hydroxide and a sulfide, optionally under phase transfer catalysis or addition of a solubiliser, with a ketone or an aldehyde of formula (III) wherein R4 and R5 can represent a C1-C12 alkyl radical or a C6-C20 aryl radical or one of the two radicals H, or R4 and R5 together form a C4-C7 ring, to form the compound of formula (IV), that b) reacts with HCN to form the corresponding nitrile, whereupon c) the crystallised nitrile is converted, by selective hydrolysis by means of a mineral acid, into the corresponding amide of formula (VI), and d) is then converted into the corresponding chiral amide of formula (VI*) by means of an L amidase or a chiral dissociating acid, whereupon by reaction with an acid, the desired chiral mercapto amino acid of formula (I) is obtained, or e) first the reaction with an acid is carried out, and then the conversion into the chiral mercapto amino acid takes place.

    Process for transition metal-catalyzed asymmetric hydrogenation of acrylic acid derivatives, and a novel catalyst system for asymmetric transition metal catalysis
    8.
    发明授权
    Process for transition metal-catalyzed asymmetric hydrogenation of acrylic acid derivatives, and a novel catalyst system for asymmetric transition metal catalysis 有权
    用于过渡金属催化的丙烯酸衍生物的不对称氢化方法，以及用于不对称过渡金属催化的新型催化剂体系

    公开(公告)号：US07473792B2

    公开(公告)日：2009-01-06

    申请号：US11666922

    申请日：2005-12-05

    申请人： Jeroen Boogers ,  Ulfried Felfer ,  Martina Kotthaus ,  Andreas H. M. De Vries ,  Johannes G. De Vries ,  Laurent Lefort ,  Gerhard Steinbauer

    发明人： Jeroen Boogers ,  Ulfried Felfer ,  Martina Kotthaus ,  Andreas H. M. De Vries ,  Johannes G. De Vries ,  Laurent Lefort ,  Gerhard Steinbauer

    IPC分类号： C07F15/00 ,  B01J31/00 ,  C07C57/02

    CPC分类号： C07C51/36 ,  B01J31/1865 ,  B01J31/187 ,  B01J31/24 ,  B01J2231/645 ,  B01J2531/821 ,  B01J2531/822 ,  B01J2531/827 ,  C07B53/00 ,  C07C67/303 ,  C07C57/36 ,  C07C57/58 ,  C07C53/128 ,  C07C59/64

    摘要： A process for transition metal-catalyzed, asymmetric hydrogenation of acrylic acid derivatives of the formula (I) in which R1 is H or an optionally substituted alkyl, aryl or heteroaryl radical, R2 is an optionally substituted alkyl, aryl or heteroaryl radical, and R3 is H or a C1-C6-alkyl radical, which comprises hydrogenating compounds of the formula (I), optionally in a solvent, in the presence of one or more hydrogen donors, using a catalyst system which comprises a transition metal from the group of ruthenium, rhodium and iridium and a combination of a chiral phosphorus ligand of the formula (II) in which Cn, together with the two oxygen atoms and the phosphorus atom, forms an optionally substituted ring having from 2 to 6 carbon atoms and R4 is an optionally substituted alkyl, aryl, alkoxy or aryloxy radical or NR5R6 where R5 and R6 may each independently be H or an optionally substituted alkyl, aryl, aralkyl or alkaryl radical, or, together with the nitrogen atom, may form a ring, and an achiral phosphine ligand of the formula (III) in which R is an optionally substituted alkyl or aryl radical, to the corresponding compounds of the formula (IV) in which R1, R2 and R3 are each as defined above, and also a novel catalyst system for asymmetric transition metal catalysis.

    摘要翻译： R 1为H或任选取代的烷基，芳基或杂芳基的式（I）的丙烯酸衍生物的过渡金属催化不对称氢化的方法，R 2为任选取代的烷基，芳基或杂芳基，R 3为 是H或C 1 -C 6烷基，其包括在一个或多个氢供体存在下，任选地在溶剂中使式（I）化合物氢化，使用包含过渡金属 钌，铑和铱以及式（II）的手性磷配体的组合，其中Cn与两个氧原子和磷原子一起形成任选取代的具有2至6个碳原子的环，R 4是 任选取代的烷基，芳基，烷氧基或芳氧基或NR5R6，其中R5和R6各自独立地为H或任选取代的烷基，芳基，芳烷基或烷芳基，或与氮原子一起形成 g和其中R是任选取代的烷基或芳基的式（III）的非手性膦配体与相应的式（IV）化合物反应，其中R 1，R 2和R 3各自如上所定义，以及 一种用于不对称过渡金属催化的新型催化剂体系。

    Process for Transition Metal-Catalyzed Asymmetric Hydrogenation of Acrylic Acid Derivatives, and a Novel Catalyst System for Asymmetric Transition Metal Catalysis
    10.
    发明申请
    Process for Transition Metal-Catalyzed Asymmetric Hydrogenation of Acrylic Acid Derivatives, and a Novel Catalyst System for Asymmetric Transition Metal Catalysis 有权
    过渡金属催化非对称氢化丙烯酸衍生物的方法，以及用于不对称过渡金属催化的新型催化剂体系

    公开(公告)号：US20070293691A1

    公开(公告)日：2007-12-20

    申请号：US11666922

    申请日：2005-12-05

    申请人： Jeroen Boogers ,  Ulfried Felfer ,  Martina Kotthaus ,  Andreas H.M. De Vries ,  Johannes De Vries ,  Laurent Lefort ,  Gerhard Steinbauer

    发明人： Jeroen Boogers ,  Ulfried Felfer ,  Martina Kotthaus ,  Andreas H.M. De Vries ,  Johannes De Vries ,  Laurent Lefort ,  Gerhard Steinbauer

    IPC分类号： C07C57/07 ,  B01J31/24 ,  C07F17/02 ,  C07B53/00

    CPC分类号： C07C51/36 ,  B01J31/1865 ,  B01J31/187 ,  B01J31/24 ,  B01J2231/645 ,  B01J2531/821 ,  B01J2531/822 ,  B01J2531/827 ,  C07B53/00 ,  C07C67/303 ,  C07C57/36 ,  C07C57/58 ,  C07C53/128 ,  C07C59/64

    摘要： A process for transition metal-catalyzed, asymmetric hydrogenation of acrylic acid derivatives of the formula (I) in which R1 is H or an optionally substituted alkyl, aryl or heteroaryl radical, R2 is an optionally substituted alkyl, aryl or heteroaryl radical, and R3 is H or a C1-C6-alkyl radical, which comprises hydrogenating compounds of the formula (I), optionally in a solvent, in the presence of one or more hydrogen donors, using a catalyst system which comprises a transition metal from the group of ruthenium, rhodium and iridium and a combination of a chiral phosphorus ligand of the formula (II) in which Cn, together with the two oxygen atoms and the phosphorus atom, forms an optionally substituted ring having from 2 to 6 carbon atoms and R4 is an optionally substituted alkyl, aryl, alkoxy or aryloxy radical or NR5R6 where R5 and R6 may each independently be H or an optionally substituted alkyl, aryl, aralkyl or alkaryl radical, or, together with the nitrogen atom, may form a ring, and an achiral phosphine ligand of the formula (III) in which R is an optionally substituted alkyl or aryl radical, to the corresponding compounds of the formula (IV) in which R1, R2 and R3 are each as defined above, and also a novel catalyst system for asymmetric transition metal catalysis.

    摘要翻译： R 1为H或任选取代的烷基，芳基或杂芳基的式（I）的丙烯酸衍生物的过渡金属催化不对称氢化的方法，R 2为任选取代的烷基，芳基或杂芳基，R 3为 是H或C 1 -C 6 - 烷基，其包括任选地在溶剂中，在一种或多种存在下将式（I）的化合物氢化 氢供体，使用包含来自钌，铑和铱的过渡金属的催化剂体系和式（II）的手性磷配体的组合，其中Cn与两个氧原子和磷原子一起， 形成具有2至6个碳原子的任选取代的环，R 4是任选取代的烷基，芳基，烷氧基或芳氧基或NR 5 R 6，其中R 5和R 6可各自独立地为H或任选取代的烷基，芳基，芳烷基或烷芳基， 或者连同硝化 可以形成环，和其中R是任选取代的烷基或芳基的式（III）的非手性膦配体与其中R 1，R 2和R 3各自相应的式（Ⅳ）化合物反应 如上所定义，以及用于不对称过渡金属催化的新型催化剂体系。