Chiral di- and triphosphites
AssigneeStudiengesellschaft Kohle mbH
InventorsManfred Reetz, Andreas Meiswinkel, Gerlinde Mehler
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Abstract
The invention claims chiral di- and triphosphites of general formulas (I) or (II), which are bridged by suitable groups. The claimed compounds can be used in asymmetric transition metal catalysis and as chiral transition metal catalysts.
Claims13
A chiral compound with the formula I or II
- in which
- L1, L2, L3, L4, L1′, L2′, L3′, L4′, L5 and L6 may each be the same or different and at least one of L1, L2, L3 and L4 in formula I or at least one of L1′, L2′, L3′, L4′, L5 and L6 in formula II is a chiral radical, where L1 and L2, L3 and L4, L1′ and L2′, L3′ and L4′, and L5 and L6 may be joined together,
- Y1, Y2, Y3, Y4, Y5, Y6, Y1′, Y2′, Y3′, Y4′, Y5′, Y6′, Y7, Y8, Y9 may be the same or different and are each O, S or an NR′ group in which R′ is hydrogen, optionally substituted C1-C6-alkyl or optionally substituted aryl, R1 and R2 are each optionally substituted C2-C22-alkylene, and
- m and m′ are each between 1 and 1000,
- with the proviso that, when one of Y5 and Y6 is O and the other is N(CH2CH3) and the L1Y1 and L2Y2 groups and L3Y3 and L4Y4 groups in each case together form a binol radical and m is equal to 1, R1 is not ethylene, and
- when Y5 and Y6 are each O and the L1Y1 and L2Y2 groups and L3Y3 and L4Y4 groups in each case together form a binol radical, m is not 4 or 5, and
- when the Y5—[R1Y6]m moiety in the compound with the formula I is —N(CH3)—C2H4—N(CH3), —N(CH(CH3)2)—C3H6—N(CH(CH3)2) or —N(CHPhCH3)—C3H6—N(CHPhCH3), the L1Y1 and L2Y2 groups and L3Y3 and L4Y4 groups do not in each case together form a binol radical.
A catalyst comprising transition metal complexes of chiral compounds having the formula I and/or II
- in which
- L1, L2, L3, L4, L1′, L2′, L3′, L4′, L5 and L6 may each be the same or different and at least one of L1, L2, L3 and L4 in formula I or at least one of L1′, L2′, L3′, L4′, L5 and L6 in formula II is a chiral radical, where L1 and L2, L3 and L4, L1′ and L2′, L3′ and L4′, and L5 and L6 may be joined together,
- Y1, Y2, Y3, Y4, Y5, Y6, Y1′, Y2′, Y3′, Y4′, Y5′, Y6′, Y7, Y8, Y9 may be the same or different and are each O, S or an NR′ group in which R′ is hydrogen or optionally substituted C1-C6-alkyl or optionally substituted aryl,
- R1 and R2 are each optionally substituted C2-C22-alkylene, and
- m and m′ are each between 1 and 1000.
A process for preparing transition metal catalysts comprising transition metal complexes of chiral compounds with the formula Ia and/or IIa comprising reacting transition metal salts with chiral compounds with the formulae I and/or II.
A process for preparing chiral compounds in which the prochiral precursor selected from olefins, ketones or ketimines is subjected in the presence of a transition metal catalyst to hydrogenation, hydroboration or hydrocyanation, 1,4 addition, hydroformylation, hydrosilylation, hydrovinylation and Heck reactions, wherein the transition metal catalyst has ligands which are selected from compounds with the general formulae I and/or II.
Dependencies are inferred from the claim text.