Infoscience

Patent

Preparation of asymmetrically substituted biaryldiphosphines and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation

Asym. substituted biaryldiphosphine ligands I (R1 = C1-6-alkyl or C3-10-cycloalkyl optionally substituted with one or more halogen atoms; R2 and R3 are equal and are C5-10-cycloalkyl or C1-6-alkyl, or R2 is C5-10-cycloalkyl or C1-6-alkyl, and R3 is aryl optionally substituted with one or more substituents selected from the group consisting of halogen atoms, nitro, amino, C1-6-alkyl, C1-6-alkoxy and di-C1-6-alkylamino groups, and each C1-6-alkyl, C1-6-alkoxy, di-C1-6-alkylamino and C5-10-cycloalkyl group in R2 and R3 optionally being substituted with one or more halogen atoms, from 2,2',6,6'-tetra-bromobiphenyl) were prepd. by a sequence of bromine-metal exchanges and subsequent reactions. Thus, lithiation of 2',6-dibromo-2-methoxy-1,1'-biphenyl (prepn. given) with BuLi followed by phosphination with chlorodicyclohexylphosphine in THF gave 74% title compd., 2',6-bis(dicyclohexylphosphino)-2-methoxy-1,1'-biphenyl (ligand 1). RuCl3/(-)ligand 1 catalyzed enantioselective hydrogenation of Et acetoacetate gave (R)-Et 3-hydroxybutyrate. [on SciFinder (R)]

    Keywords: Phosphines Role: CAT (Catalyst use) ; SPN (Synthetic preparation) ; PREP (Preparation) ; USES (Uses) (diphosphines ; biaryldiphosphines; prepn. of asym. substituted biaryldiphosphines and their use as cocatalysts for transition metal catalyzed enantioselect ; asym biaryl diphosphine prepn cocatalyst asym hydrogenation; ruthenium rhodium biaryldiphosphine catalyzed asym hydrogenation

    Note:

    CAN 144:129105

    29-7

    Organometallic and Organometalloidal Compounds

    Patent

    written in English.

    20060112

    10049-08-8 (Ruthenium trichloride); 35138-22-8; 37366-09-9; 52462-29-0 Role: CAT (Catalyst use), USES (Uses) (prepn. of asym. substituted biaryldiphosphines and their use as cocatalysts 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 and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation); 871915-66-1P; 871915-67-2P; 871915-68-3P; 871915-69-4P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (prepn. of asym. substituted biaryldiphosphines and their use as cocatalysts 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 and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation); 19821-80-8P (1,3-Dibromo-2-iodobenzene); 97038-96-5P; 507241-82-9P; 873110-78-2P; 873110-79-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of asym. substituted biaryldiphosphines and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation); 152578-86-4 Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of asym. substituted biaryldiphosphines and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation); 2018-61-3P; 3618-96-0P; 17480-69-2P; 22644-27-5P; 24915-95-5P; 86728-85-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of asym. substituted biaryldiphosphines and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation)

    A1

    EP

    2004-14908

    20040625

    Reference

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

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