Chiral aminophosphines

Details Chiral aminophosphines Chiral aminophosphines

1997-12-10

1999-07-06

Burn, Brian M.

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

Organic compounds

Amino nitrogen containing

C07C21150

Patent

active

059199814

ABSTRACT:
This invention relates to (R)- and (S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (R-1 and S-1) and (R)- and (S)-2,2'-bis(diarylphospinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binap hthyl (R-2 and S-2) and (R)- and (S)-2,2'-bis(dialkylphospinoamino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bina phthyl (R-3 and S-3); to a process for the preparation of R-1 and S-1 in which (R) or (S)-1,1'-binaphthyl-2,2'-diamine is partially hydrogenated in the presence of Adam's catalyst (5-20 wt % of starting material) at 20-100.degree. C. for 20-100 hours in glacial acetic acid (solvent); to a process for the preparation of R-2, S-2, R-3 and S-3 in which R-1 or S-1 is reacted with chlorodiarylphosphine or chlorodialkylphosphine in the presence of n-butyllithium; and to the rhodium complexes containing 2 or 3 as effective catalysts for the asymmetric hydrogenation of prochiral substrates such as olefins to produce higher valued chiral products; and to the asymmetric catalytic hydrogenation of enamides under mild conditions using the Rh-(2) or Rh-(3) as catalyst with chemical yields as high as 100% and enantiomeric excess (e.e.) as high as 99%.

REFERENCES:
Kagan et al., "Reduction Asymetrique Catalysee Par Des Complexes De Metaux De Transition", Journal of Organometallic Chemistry, vol. 90, 1975, pp. 353-365. (+) Diop!*C10.sub.4 -", Journal of Organometallic Chemistry, vol. 114, 1976, pp. 325-337.
Samuel et al., "Phellanphos and Nopaphos, New Diphosphines for Asymmetric Catalysis", Nouveau Journal De Chimie, vol. 5, No. 1, 1981, pp. 15-20.
Burk et al., "A Convenient Asymmetric Synthesis of .alpha.-1-Arylalkylamines through the Enantioselective Hydrogenation of Enamides", J. Am. Chem. Soc., vol. 118, 1996, pp. 5142-5143.

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