Optically active chiral diphosphine ligands

Details Optically active chiral diphosphine ligands Optically active chiral diphosphine ligands

2003-01-31

2004-09-21

Nazario-Gonzalez, Porfirio (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

C556S023000, C568S008000, C502S170000, C502S171000, C502S169000, C585S250000, C585S275000

Reexamination Certificate

active

06794525

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to the use of chiral diphosphines as optically active ligands for the preparation of diphosphino-metal complexes. The invention also pertains to the diphosphino-metal complexes comprising a chiral diphosphine as ligand and the asymmetric catalysis processes employing these complexes. The invention envisages more particularly the use of these diphosphino-metal complexes in asymmetric hydrogenation or isomerization processes for the synthesis of organic products of specified chirality.
BACKGROUND
Known in the prior art are different ligands used for the synthesis of diphosphino-metal complexes having catalytic properties in asymmetric hydrogenation. One can cite, e.g., the compound BINAP described by the Takasago company in European patent applications nos. 444 930 and 295 109, the compound MeOBIPHEP described by the Hoffmann-La Roche company in European patent application no. 398132 and PCT application No. WO 93/15090.
SUMMARY OF THE INVENTION
This invention relates to an (R) or (S) chiral diphosphine of formula (I):
wherein R and R1, which can be identical or different, represent an optionally saturated C
1-10
alkyl group, an optionally saturated C
3-9
cycloalkyl group, a C
5-10
aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C
1-5
alkoxy, an amino such as NH
2
, NHR
4
, N(R
4
)
2
, a sulfino, a sulonfyl, with R
4
representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms or R and R1 together represent an optionally saturated C
2-6
substituted alkyl group, an optionally saturated C
3-9
cycloalkyl group, a C
5-10
aryl group, the cycloalkyl or aryl groups being optionally substituted by a C
1-5
alkyl, a halogen, a hydroxy, a C
1-5
alkoxy, an amino, a sulfino, a sulonfyl, with R
4
representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, R2 and R3, which can be identical or different, represent an optionally saturated C
3-8
cycloalkyl group, a C
6-10
aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C
1-5
alkoxy, an amino, a sulfino, a sulonfyl, with R
4
representing an alkyl, an alkoxy or an alkylcarbonyl, the cycloalkyl, aryl groups optionally including one or more heteroatoms, or R2 and R3 together form an optionally saturated C
4-8
cyclic group, a C
6-10
aryl group, the groups being carefully substituted by a halogen, a hydroxy, a C
1-5
alkoxy, an amino, a sulfino, a sulonfyl, with R
4
representing an alkyl, an alkoxy or an alkylcarbonyl, the cyclic and aryl groups optionally including one or more heteroatoms.


REFERENCES:
patent: 0 647 648 (1995-04-01), None
patent: 1 002 801 (2000-05-01), None
patent: WO 93/15089 (1993-08-01), None
patent: WO 93/15090 (1993-08-01), None
patent: WO 01/21625 (2001-03-01), None

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