Structural requirements in chiral diphosphine-rhodium complexes-XII1 1 Part XI. R. Glaser, S. Geresh, J. Blumenfeld and M. Twaik, Tetrahedron 34, 2405 (1978). Asymmetric homogeneous hydrogenation of Z-α-N-methylacetamidocinnamic acid and methyl ester catalyzed by rhodium(I) complexes of DIOP and its carbocyclic analogues

Robert Glaser, Shimona Geresh, Menachem Twaik, N. Leo Benoiton

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Abstract

Z-α-N-methylacetamidocinnamic acid and its methyl ester were hydrogenated with rhodhim(I) complexes containing (2R, 3R)-O-2,3-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (DIOP) or its carbocyclic analogues: (1R,2R)-trans-1,2-bis(diphenylphosphinomethyl)cyclobutane or (1S,2S)-trans-1,2-bis(diphenylphosphinomethyl) cyclohexane. The N-acetyl-N-methylphenylalanine methyl ester reaction product was formed with an optical purity of 73% ee-(R) [(2R, 3R)-DIOP]; 43% ee-(R) [(1R, 2R)-cyclobutane analogue]; and 26% ee-(R) [(1S,2S])-cyclohexane analogue]. Similarly, N-acetyl-N-methylphenylalanine was formed with an optical purity of 87% ee-R [(2R, 3R)-DIOP] and 68% ee-(R) [(1R, 2R)-cyclobutane analogue].

Original languageEnglish
Pages (from-to)3617-3621
Number of pages5
JournalTetrahedron
Volume34
Issue number24
DOIs
StatePublished - 1 Jan 1978

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