Infoscience

Patent

Preparation of asymmetrically substituted biaryldiphosphines as ligands for enantioselective hydrogenation

Provided is a process for prepn. of asym. substituted biaryldiphosphine ligands I (R1 = C1-6-alkyl, C3-10-cycloalkyl optionally substituted with one or more halogen atoms; R2, R3 = aryl, C5-10-cycloalkyl, C1-6-alkyl, or R2 = C5-10-cycloalkyl, C1-6-alkyl; R3 = aryl optionally substituted with one or more substituents selected from the group consisting of halo, nitro, amino, C1-6-alkyl, C1-6-alkoxy, and di-C1-6-alkylamino groups, and each C1-6-alkyl, C5-10-cycloalkyl, C1-6-alkoxy and di-C1-6-alkylamino group in R2 and R3 optionally being substituted with one or more halogen atoms, from 2,2',6,6'-tetrabromobiphenyl) by a sequence of bromine metal exchanges and subsequent reactions. Thus, phosphination of 2,6,6-tribromo-2'-methoxy-1,1'-biphenyl (prepn. given) with Ph2PCl followed by isomerization gave 2',6-bis(diphenylphosphinyl)-2-methoxy-1,1'-biphenyl (ligand 1); RuCl3/(+)-ligand 1-catalyzed hydrogenation of Et acetoacetate in EtOH at 50 Deg gave (S)-Et 3-hydroxybutyrate in 6h. [on SciFinder (R)]

    Keywords: Phosphines Role: CAT (Catalyst use) ; SPN (Synthetic preparation) ; PREP (Preparation) ; USES (Uses) (diphosphines ; biaryldiphosphines; prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation) ; asym biaryl diphosphine prepn ligand transition metal hydrogenation catalyst

    Note:

    CAN 144:129104

    29-7

    Organometallic and Organometalloidal Compounds

    Patent

    written in English.

    20060112

    10049-08-8 (Ruthenium trichloride); 12112-67-3; 35138-22-8; 37366-09-9; 52462-29-0 Role: CAT (Catalyst use), USES (Uses) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation); 871707-42-5P; 871707-44-7P Role: CAT (Catalyst use), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), USES (Uses), RACT (Reactant or reagent) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation); 871915-66-1P; 871915-67-2P; 871915-68-3P; 871915-69-4P; 871915-70-7P; 871915-71-8P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation); 100-46-9 (Benzylamine); 108-36-1 (1,3-Dibromobenzene); 141-97-9 (Ethyl acetoacetate); 617-52-7 (Dimethyl itaconate); 638-07-3 (Ethyl 4-chloro-3-oxobutyrate); 1079-66-9 (Chlorodiphenylphosphine); 5469-45-4; 14428-98-9; 16523-54-9 (Chlorodicyclohexylphosphine); 52386-78-4 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation); 19821-80-8P (1,3-Dibromo-2-iodobenzene); 97038-96-5P (2,2',6,6'-Tetrabromo-1,1'-biphenyl); 871707-37-8P; 871707-41-4P; 871707-43-6P; 873110-78-2P; 873110-79-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation); 152578-86-4 Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation); 2018-61-3P; 3618-96-0P; 10172-89-1P; 17480-69-2P; 22644-27-5P; 24915-95-5P; 38235-77-7P; 56816-01-4P; 86728-85-0P; 90866-33-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of asym. substituted biaryldiphosphines as ligands for transition metal catalyzed enantioselective hydrogenation)

    A1

    EP

    2004-14909

    20040625

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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