New phosphorous compound useful as ligand in catalyst for e.g. hydroformylation-, hydrocyanation-, carbonylation-, hydroacylation-, hydroamination- and hydro esterification reactions

    公开(公告)号:DE102006041064A1

    公开(公告)日:2007-03-08

    申请号:DE102006041064

    申请日:2006-09-01

    Applicant: BASF AG

    Abstract: Phosphorous compound (I) is new. Phosphorous compound of formula (I) is new. Y1>bivalent bridge group with bridge atoms between the flanking bonds; Ra, Rb : (cyclo)alkyl, heterocycloalkyl or (het)aryl (where alkyl is substituted by 1-5 (hetero)cycloalkyl, (het)aryl,(cyclo)alkoxy, heterocycloalkoxy, (het)aryloxy, OH, SH, polyalkyleneoxide, polyalkylene imine, COOH, carboxylate, SO3H, sulfonate, NE1>E2>, NE1>E2>E3>X->, halo, NO2, acyl or CN), where (hetero)cycloalkyl- and (het)aryl are substituted with 1-5 alkyl; or RaRb+P+X1>X2>5-8 membered heterocycle, optionally substituted with 1-3 (hetero)cycloalkyl or (het)aryl, where heterocycle and the substituted group consists of 1-4 of (cyclo)alkyl, heterocycloalkyl, (het)aryl, OH, SH, polyalkylene oxide, polyalkylene imine, alkoxy, halo, COOH, carboxylate, SO3H, sulfonate, NE4>E5>, NE4>E5>E6>X-, NO2, alkoxycarbonyl, acyl or CN; E1>-E8>H, (cyclo)alkyl or aryl; X->anion; Ry : peptide group comprising at least two amino acid units; X1>, X2>O, S, SiRcRd or NRe; Z : NR9> or CR9>R10>; Rc, Rd, Re : H, (cyclo)alkyl, heterocycloalkyl or (het)aryl; R1>-R10>H, (cyclo)alkyl, heterocycloalkyl, (het)aryl, OH, SH, polyalkylene oxide, polyalkylene imine, alkoxy, halo, SO3H, sulfonate, NE7>E8>, alkylene-NE7>E8>, CF3, NO2, alkoxycarbonyl, carboxyl, acyl or CN; or two adjacent groups of R1>, R2>, R4>, R6>, R8>, R9> (for a bonding portion of double bond between the ring atoms) : six membered ring exhibiting a maximum of three non-cumulative double bonds; and a, b, c : 0 or 1. Independent claims are also included for: (1) a catalyst comprising at least a complex having a transition metal and (I) as ligand; (2) a method for hydroformylating a compound containing at least an ethylenic unsaturated double bond comprising reacting the ethylenic unsaturated double bond with carbon monoxide and hydrogen in the presence of the catalyst; and (3) a method for the preparation of chiral compounds comprising reacting the prochiral compound containing at least an ethylenic unsaturated double bond with a substrate in the presence of a chiral catalyst. [Image].

    Preparation of optically active 3-phenylpropionic acid derivatives, used for preparing halo-phenyl compounds, comprises hydrogenating cis-isomer mixture of phenyl compound, crystallizing enantiomer mixture and isolating solid material

    公开(公告)号:DE102005029228A1

    公开(公告)日:2006-12-28

    申请号:DE102005029228

    申请日:2005-06-23

    Applicant: BASF AG

    Abstract: Preparation of an optically active 3-phenylpropionic acid derivative (I) comprises: (a) an enantioselective hydrogenation of a cis-isomer or cis/trans-isomer mixture of a phenyl compound (II) in the presence of a chiral hydrogenation catalyst to give an enantiomer enriched enantiomer mixture; (b) crystallization of the enantiomer enriched enantiomer mixture by supplementation of a basic salt former in a solvent and isolating the stereoisomer enriched solid material; and (c) optionally isolation of the protonated isomer or a substitutional cation. Preparation of an optically active 3-phenylpropionic acid derivative of formula (I) comprises: (a) an enantioselective hydrogenation of a cis-isomer or cis/trans-isomer mixture of a phenyl compound of formula (II) in the presence of a chiral hydrogenation catalyst to give an enantiomer enriched enantiomer mixture; (b) crystallization of the enantiomer enriched enantiomer mixture by supplementation of a basic salt former in a solvent and isolating the stereoisomer enriched solid material; and (c) optionally isolation of the protonated isomer or a substitutional cation. R 1>-R 4>H, 1-6C alkyl, halo-1-6C alkyl, OH-1-6C alkyl, 1-6C alkoxy, OH-1-6C alkoxy, 1-6C alkoxy-1-6C alkyl, OH-1-6C alkoxy-1-6C alkyl, 1-6C alkoxy-1-6C alkoxy or OH-1-6C alkoxy-1-6C alkoxy; R 5>1-6C alkyl, 5-8C cycloalkyl, phenyl or benzyl; and A : H or cationic equivalent. Independent claims are also included for: (1) the preparation of optically active halo-phenyl compound of formula (III), which comprises protonating (I) in to an acid; reducing the acids or the metal salts to give an alcohol compound of formula (IV); and halodehydroxylating (IV); and (2) an optically active compound 3-phenylpropionic acid derivative (I). Hal : Cl, Br or I. [Image] [Image].

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