A highly efficient asymmetric synthesis of methoxyhomophenylalanine using Michael addition of phenethylamine

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9019-9022

  Yamada, Masahiko ^a   Nagashima, Nobuo ^a   Hasegawa, Junzo ^a   Takahashi, Satomi ^a  

^a KANEKA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHENETHYLAMINE DERIVATIVE; PHENYLALANINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; HYDROGENATION; MICHAELIS CONSTANT; NONHUMAN;

EID: 0032481014     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02023-1     Document Type: Article

References (30)

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19. 6. The (1S, αS) configuration of 4a was determined by conversion into known (S)-p-methoxyhomophenylalanine 1 through hydrogenolysis; see text.
20. 7. The d.e. values of the Michael adducts were readily determined by a reverse phase HPLC analysis using JASCO Finepak SIL C18-5 column by using pH 2.5 phosphate buffer-CH3CN=8:2 (v/v).
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30. 1H NMR measurements of the reaction mixtures at appropriate time intervals have indicated that the order of the hydrogenation reaction rates may be roughly estimated to be PhCH(Me)-NH > C=O.