Phosphine ligands

A transition metal complex of formula II

• MmLnXpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 43
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is an optional double bond;
• R1 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I;
• X is a coordinating anion,
• m, n and p are each 1, and
• q is 0, if M is Rh.

A transition metal complex of formula II

• MmLnXp II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 44
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocydic ring;
• dotted line is an optional double bond;
• R1 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is acyloxy,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Ru.

A transition metal complex of formula II

• MmLnXpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 45
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8 are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is Cl,
• m and n are each 2,
• p is 4,
• q is 1, and
• A is triethylamine, if M is Ru.

A transition metal complex of formula II

• MmLnXpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 46
• I, wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a π-methallyl group,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Ru.

A transition metal complex of formula II

• MmLnXpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 47
• I, wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a coordinating anion,
• m, n and p are each 1, and
• q is 0, if M is Ir.

A transition metal complex of formula II

• MmLnXpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 48
• I, wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cydoalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is Cl,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Pd.

A transition metal complex of formula II

• MmLnXvpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 49
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• S is Cl, Br or I,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Ni.

A transition metal complex of formula

• MmLnXpAq II
• wherein
• M is Rh,
• L is the diphosphine compound the formula I
• 50
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a coordinating anion,
• m, n and p are each 1, and
• q is 0.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is a transition metal,
• L is the diphosphine compound of the formula I
• 51
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2 —R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R1 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a diene ligand,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, if M is Rh.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is for a transition metal,
• L is the diphosphine compound of formula I
• 52
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is an olefinic ligand,
• D is a non-coordinating anion,
• m, n and r are each 1,
• p is 2 and
• q is 0, if M is Rh.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is a transition metal,
• L is the diphosphine compound of the formula I
• 53
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is Cl, Br or I,
• A is benzene or p-cymene,
• D is Cl, Br or I, and
• m, n, p, q and r are each 1, if M is Ru.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is for a transition metal,
• L is for the diphosphine compound of formula I
• 54
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• D is a non-coordinating an ion,
• m and n are each 1,
• p and q are each 0, and
• r is 2, if M is Ru.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is for a transition metal,
• L is for the diphosphine compound of the formula I
• 55
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a diene ligand,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, if M is Ir.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is for a transition metal,
• L is the diphosphine compound of the formula I
• 56
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is an olefinic ligand,
• D is a non-coordinating anion,
• m, p and r are each 1,
• n is 2 and
• q is 0, if M is Ir.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I
• 57
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I.
• X is a n-allyl group,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, if M is Pd.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is for Rh,
• L is for the diphosphine compound of the formula I
• 58
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3—, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I, and
• wherein
• X is a diene ligand,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0.

A metal complex of formula

• [MmLnXpAq]Dr III
• wherein
• M is for Rh,
• L is for the diphosphine compound of the formula I
• 59
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is an olefinic ligand,
• D is a non-coordinating anion,
• m, n and r are each 1,
• p is 2 and
• q is 0.

An optical active compound of formula 6

• 60
• wherein R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is absent or is present and forms a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl.

A process for the asymmetric hydrogenation of a prochiral olefinic or ketonic compound wherein the reaction is carried out in presence of metal complex of fomula II

• MmLnXpAq II
• wherein
• M is a transition metal,
• L is the diphosphine compound of the formula I
• 61
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R5 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a coordinating anion,
• m, n and p are each 1, and
• q is 0, if M is Rh, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I,
• X is acyloxy,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Ru, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I,
• X is Cl,
• m and n are each 2,
• p is 4,
• q is 1, and
• A is triethylamine, if M is Ru, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I,
• X is a π-methallyl group,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Ru, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I,
• X is a coordinating anion,
• m, n and p are each 1, and
• q is 0, if M is Ir, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I,
• X is Cl,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Pd, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I,
• X is Cl, Br or I,
• m and n are each 1,
• p is 2, and
• q is 0, if M is Ni, or
• wherein
• M is Rh,
• L is the diphosphine compound of formula I;
• X is a coordinating anion,
• m, n and p are each 1, and
• q is 0.

A process for the asymmetric hydrogenation of a prochiral olefinic or ketonic compound wherein the reaction is carried out in presence of metal complex of formula III

• [MmLnXp]Dr III
• wherein
• M is a transition metal,
• L is the diphosphine compound of the formula I
• 62
• wherein
• R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3−, —CO—NR8R8′, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl;
• R3 is alkyl, cycloalkyl, aryl or heteroaryl;
• R4′ and R4 is independently of each other hydrogen, alkyl or optionally substituted aryl;
• or
• R4′ and R4 together, with the C-atom they are attached, form a 3-8-membered carbocyclic ring;
• dotted line is optionally a double bond;
• R1 and R6 are independently of each other hydrogen, alkyl or aryl;
• R7 is alkyl, aryl or NR8R8′;
• and
• R8 and R8′ are independently of each other hydrogen, alkyl or aryl;
• the substituents R3 on the phospholane phophorus atom and the substituent on the C2 atom of the phospholane ring are in cis relation to each other as indicated by the bold bonds in formula I,
• X is a diene ligand,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, if M is Rh, or
• wherein
• M is for a transition metal,
• L is the diphosphine compound of formula I,
• X is an olefinic ligand,
• D is a non-coordinating anion,
• m, n and r are each 1,
• p is 2 and
• q is 0, if M is Rh, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I;
• X is Cl, Br or I,
• A is benzene or p-cymene,
• D is Cl, Br or I, and
• m, n, p, q and r are each 1, if M is Ru, or
• wherein
• M is for a transition metal,
• L is for the diphosphine compound of formula I,
• D is a non-coordinating anion,
• m and n are each 1,
• p and q are each 0, and
• r is 2, if M is Ru, or
• wherein
• M is for a transition metal,
• L is for the diphosphine compound of formula I,
• X is a diene ligand,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, if M is Ir, or
• wherein
• M is for a transition metal,
• L is the diphosphine compound of formula I,
• X is an olefinic ligand,
• D is a non-coordinating anion,
• m, p and r are each 1,
• n is 2 and
• q is 0, if M is Ir, or
• wherein
• M is a transition metal,
• L is the diphosphine compound of formula I;
• X is a 7-allyl group,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, if M is Pd, or
• wherein
• M is for Rh,
• L is for the diphosphine compound of formula I,
• X is a diene ligand,
• D is a non-coordinating anion,
• m, n, p and r are each 1, and
• q is 0, or
• wherein
• M is for Rh,
• L is for the diphosphine compound of formula I,
• X is an olefinic ligand,
• D is a non-coordinating anion,
• m, n and r are each 1,
• p is 2 and
• q is 0.