Asymmetric Hydrogenation of 3, 4-Methylenedioxy-α-acetamidocinnamic Acid Using Newly Developed Silica Gel-Supported Chiral Rhodium (I) -Phosphine Complexes

Asymmetric Hydrogenation of 3, 4-Methylenedioxy-α-acetamidocinnamic Acid Using Newly Developed Silica Gel-Supported Chiral Rhodium (I) -Phosphine Complexes

The asymmetric hydrogenation of 3, 4-methylenedioxy-α-acetamidocinnamic acid was carried out in the presence of a chiral Rh (I) -complex of (2S, 4S) -N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (BPPM) adsorbed on hydrophobic silica gel in MeOH- H2O solvents. Excellent c...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1987/05/25, Vol.35(5), pp.1686-1690
Hauptverfasser: ISHIZUKA, NAOYASU, TOGASHI, MASAHIRO, INOUE, MASAMI, ENOMOTO, SABURO
Format: Artikel
Sprache:eng
Schlagworte:
3, 4-methylenedioxy-α-acet-amidocinnamic acid
asymmetric hydrogenation
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
L-DOPA
Organic chemistry
Preparations and properties
rhodium complex
silica gel
solid catalyst
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Zusammenfassung:The asymmetric hydrogenation of 3, 4-methylenedioxy-α-acetamidocinnamic acid was carried out in the presence of a chiral Rh (I) -complex of (2S, 4S) -N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (BPPM) adsorbed on hydrophobic silica gel in MeOH- H2O solvents. Excellent conversions (100%) and a high optical yield (85%) were attained with [Rh (COD) BPPM] +ClO4- on methylated silica gel. The adsorption of the complex was improved byintroducing a stearoyl group instead of the butoxycarbonyl group of BPPM. When the recovered catalysts were reused three times, the optical yields decreased gradually from 85 to 69%.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.35.1686