Chiral ligand

Details Chiral ligand Chiral ligand

2002-03-14

2004-07-13

Ramsuer, Robert W. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06762306

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a chiral transition metal complex, which is useful as a catalyst for converting a prochiral unsaturated organic compound to a corresponding asymmetric compound, and a process for producing the same.
BACKGROUND OF THE INVENTION
Martins et al. discloses an optically active transition metal complex catalyst having an aminophosphine-phosphinite ligand (Synlett., 1998, Vol. 10, pp1162), however, the catalyst was not always satisfactory in the asymmetric reaction of converting a carbonyl compound to a chiral alcohol compound.
Hence, a more effective catalyst that can be suitably used for industrial-scale production has been desired.
SUMMARY OF THE INVENTION
According to the present invention, an efficient catalyst for asymmetric production process is provided.
The present invention provides:
1. a chiral phosphine compound of formula (1):
wherein R
1
and R
2
independently represent
an aryl or heteroaryl group, which may be substituted,
a saturated hydrocarbon group, which may be substituted, and
Ar group independently represents
an aryl or heteroaryl group, which may be substituted,
an aryloxy group, which may be substituted,
a saturated hydrocarbon group, which may be substituted, or
Ar groups on the same phosphorus atom are bonded to form an arylene, heteroarylene or alkylene group, which may be substituted, and
* represents an asymmetric carbon atom;
2. a transition metal complex of a chiral phosphine compound of formula: (1) as defined above;
3. a process for producing a chiral phosphine compound of formula (1) as defined above, which comprises reacting an optically active azetidine alcohol compound of formula (2):
wherein R
1
, R
2
and * represent the same as defined above, with a phosphine of formula (3):
X—P(Ar)
2
  (3),
wherein X represents a leaving group (e.g. a halogen atom, or the like.)
Ar represents the same as defined above;
4. an optically active azetidine alcohol compound of formula (4):
wherein R
1
and R
2
independently represent
a saturated hydrocarbon group, which may be substituted, and
* represent the same as defined above; and
5. a process for producing an optically active organic compound, which comprises asymmetrically reducing a prochiral unsaturated compound with hydrogen in the presence of the transition metal complex of a compound of formula (1) as defined above.


REFERENCES:
Pasquier et al., Organometallics, vol. 19, No. 26, pp. 5723-5732, (2000).
Pasquier et al.,Synthetic Letters,vol. 10, pp. 1162-1164 (Oct. 1998).
Aboulhoda et al.,Tetrahedron: Asymmetry,vol. 5, No. 7, pp. 1321-1326 (1994).
Behnen et al.,Tetrahedron: Asymmetry,vol. 4, No. 7, pp. 1413-1416 (1993).

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