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Volumn 3, Issue 20, 2001, Pages 3157-3159

Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDYL ALANINE; 2-PYRIDYL ALANINE; ALANINE; ANTINEOPLASTIC ANTIBIOTIC; AZATYROSINE; BETA-(5-HYDROXY-2-PYRIDYL)ALANINE; DRUG DERIVATIVE; HYDROGEN; PYRIDINE DERIVATIVE;

EID: 0035807552     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016455q     Document Type: Article
Times cited : (36)

References (52)
  • 2
    • 0003532765 scopus 로고
    • The Chemical Society: Cambridge
    • (b) Amino Acids, Peptides and Proteins; The Chemical Society: Cambridge, 1968-1991; Vols. 1-22.
    • (1968) Amino Acids, Peptides and Proteins , vol.1-22
  • 4
    • 0000411342 scopus 로고
    • Academic Press: New York
    • (a) Roberts, D. C.; Vellaccio, F. The Peptides; Academic Press: New York, 1983; Vol. 5, pp 341-449.
    • (1983) The Peptides , vol.5 , pp. 341-449
    • Roberts, D.C.1    Vellaccio, F.2
  • 14
    • 0041370660 scopus 로고    scopus 로고
    • Japanese Patent JP 60/130591 A2, 1985
    • (a) Japanese Patent JP 60/130591 A2, 1985.
  • 15
    • 0042372399 scopus 로고    scopus 로고
    • European Patent EP 98609/A2, 1984
    • (b) European Patent EP 98609/A2, 1984.
  • 38
    • 0042372397 scopus 로고    scopus 로고
    • note
    • (2-Pyridyl)dehydroamino acid derivatives 1a-b were prepared from commercially available pyridine-2-carboxaldehyde and 5-bromo-pyridine-2-carboxaldehyde, respectively, in 78-89% yield by treatment with N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester in the presence of N,N,N′,N′-tetramethylguanidine (TMG) in THF at room temperature for 6 h.
  • 40
    • 33745336054 scopus 로고
    • For a review on the asymmetric hydrogenation using pnospnme ligands, see: Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 106-112
    • Knowles, W.S.1
  • 41
    • 0041871413 scopus 로고    scopus 로고
    • note
    • 19F NMR.
  • 42
    • 0041370646 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the newly generated chiral center in 4a using (R,R)-6 catalyst was determined to be (5) by cleavage of protective groups to the corresponding known α-amino acid and comparison of its rotation; see: ref 9a.
  • 44
  • 51
    • 0041370657 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess (% ee) of (5)-(-)-10 before and after crystallization was determined by converting to Mosher's amide in three steps: see ref 18 for details.
  • 52
    • 0041871418 scopus 로고    scopus 로고
    • note
    • Preparative reversed phase HPLC was carried out on a Waters, Symmetry, C18, 7.0 μ, 40 × 100 mm column using 2:98 MeCN/0.1% aqueous trifluoroacetic acid. 25 mL/min at 225 nm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.