Tetrahedron p. 3061 - 3070 (1999)
Update date:2022-07-29
Topics:
McCarthy, Mary
Guiry, Patrick J.
A five step synthesis of the title compound in good yield is described. The biaryl linkage was formed in a Pd-catalyzed coupling of 2-chloro-3,6- dimethylpyrazine 10 with 2-methoxy-1-naphthylboronic acid 9. Demethylation of the product ether 11 afforded alcohol 12 which was converted into the corresponding triflate 13 by treatment with triflic arthydride. A Ni- catalyzed phosphinylation gave the required phosphinamine ligand 7 as a racemate. Diastereomeric palladacycles 16, formed from 7 and (+)-di-μ- chlorobis[(R)-dimethyl(1-(1-naphthyl)ethyl)aminato-C2,N]dipalladium (II) 15 were separated, after considerable effort, to give diastereomerically pure 7. Displacement of the resolving agent by reaction with 1,2- bis(diphenylphosphino)ethane gave enantiopure 7. At ambient temperature this ligand was found to racemise.
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