Tetrahedron p. 1245 - 1253 (1984)
Update date:2022-07-30
Topics: Asymmetric Hydrogenation Atropisomeric Rh(I)-catalyzed 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) Bis(triaryl)phosphine α-(Acylamino)acrylic Acids
Miyashita, A.
Takaya, H.
Souchi, T.
Noyori, R.
Racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl has been synthesized from 2,2'-dihydroxy-1,1'-binaphthyl in two steps and resolved into optically pure (R)-(+) and (S)-(-) enantiomers by the use of (+)-di-μ-chlorobis<(S)-N,N-dimethyl-α-phenylethylamine-2C,N> dipalladium.This new axially dissymmetric bis(triaryl)phosphine serves as an excellent ligand for Rh(I)-catalyzed asymmetric hydrogenations of α-(acylamino)acrylic acids or esters.Factors controlling the enantioselectivity and mechanistic aspects are discussed on the basis of the 31P-NMR measurements.
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