Chiral phospine ligand

Details Chiral phospine ligand Chiral phospine ligand

1980-03-19

1982-05-25

Sneed, Helen M. S.

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

Organic compounds

Phosphorus containing

C07F 950

Patent

active

043318185

ABSTRACT:
The chiral phosphine ligand (R)-1,2-bis(diphenyl-phosphino)-1-cyclohexylethane, when complexed to Rh(I), functions as a superior chiral hydrogenation catalyst. The chiral phosphine ligand is more stereochemically rigid than previous compounds; consequently, virtually optically pure materials can be produced from the chiral hydrogenation of prochiral compounds using the catalyst of this invention. This catalyst is especially useful in the chiral hydrogenation of alpha-acylamido acrylic acids.

REFERENCES:
patent: 3382173 (1968-05-01), Zorn et al.
patent: 3798241 (1974-03-01), Kagan et al.
patent: 3978101 (1976-08-01), Aviron-Violet
King et al., "1,2-Bis(diphenylphosphino)-1-phenylethane: A Chiral Ditertiary Phosphine Derived from Mandelic Acid Used as a Ligand in Asymmetric Homogeneous Hydrogenation Catalysts", J. Org. Chem., vol. 44, No. 10 (1979), pp. 1729-1731.
Brown et al., "R-Phenyl Bis Diphenylphosphinoethane; Structural Studies Pertaining to Rhodium-Catalyzed Asymmetric Hydrogenation, " Tetra Let., No. 50 (1979), pp. 4859-4862.
Lauer et al, J. Organomet-Chem 177 309-312 (1979)
Vineyard et al, JACS 99 5046 (1977).
Valentine et al, Synthesis, 329-356 (1978)
Kagan et al, JACS 94 6429 (1972).
Halpern et al, J.A.C.S. 99 8055 (1977).
Fryzuk et al., J.A.C.S. 100 7556 (1978), JACS 99 6262 (1977).
Kosolopoff et al, Organic Phosphorus Compounds, Wiley Intersc., N.Y., vol. 1, pp. 202-210 (1972).

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