公开(公告)号：EP1830958B1

公开(公告)日：2011-03-09

申请号：EP05817279.2

申请日：2005-12-05

申请人： DSM Fine Chemicals Austria Nfg GmbH & Co KG

发明人： BOOGERS, Jeroen ,  FELFER, Ulfried ,  KOTTHAUS, Martina ,  DE VRIES, Andreas, H., M. ,  DE VRIES, Johannes, G. ,  LEFORT, Laurent ,  STEINBAUER, Gerhard

IPC分类号： B01J31/24 ,  C07B53/00 ,  C07C51/36

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.

公开(公告)号：EP1830958A1

公开(公告)日：2007-09-12

申请号：EP05817279.2

申请日：2005-12-05

申请人： DSM Fine Chemicals Austria Nfg GmbH & Co KG

发明人： BOOGERS, Jeroen ,  FELFER, Ulfried ,  KOTTHAUS, Martina ,  DE VRIES, Andreas, H., M. ,  DE VRIES, Johannes, G. ,  LEFORT, Laurent ,  STEINBAUER, Gerhard

IPC分类号： B01J31/24 ,  C07B53/00 ,  C07C51/36

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.

公开(公告)号：EP1242376B1

公开(公告)日：2004-06-09

申请号：EP00988767.0

申请日：2000-11-30

申请人： DSM Fine Chemicals Austria Nfg GmbH & Co KG

发明人： HENDEL, Wolfram ,  SCHWENDINGER, Karl ,  FELFER, Ulfried

IPC分类号： C07D209/34

CPC分类号： C07D209/34

摘要： The invention relates to a method for producing 2-oxindoles from the corresponding isatines of formula (I), wherein R can be H, CH3, phenyl or benzyl and R1 can be H, C1-C4-alkyl, C1-C4-alkoxy, phenyl, phenoxy, halogen, amino, nitro or hydroxy. Said isatines are converted by means of hydrazine hydrate in a polar solvent at a temperature of 15 to 185 °C to form a corresponding isatine hydrazone which directly undergoes further reaction to form the corresponding 2-oxindole of formula (II) by adding diazabicyclooctane and/or diazabicycloundecane and/or ethyldiisopropylamine as a catalyst in temperatures of 100 to 185 °C, whereby the produced reaction water is distilled off. According to formula (II), R and R1 have the aforementioned definitions. The 2-oxindole is isolated from the reaction mixture by distilling off the solvent and by means of crystallisation.