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Volumn 126, Issue 32, 2004, Pages 9918-9919

Highly efficient synthesis of β-amino acid derivatives via asymmetric hydrogenation of unprotected enamines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID DERIVATIVE; BETA AMINO ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4043110495     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047901i     Document Type: Article
Times cited : (247)

References (30)
  • 8
    • 0036739952 scopus 로고    scopus 로고
    • and references therein
    • Trost, B. M. Acc. Chem. Res. 2002, 35, 695 and references therein.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 695
    • Trost, B.M.1
  • 11
    • 0003544583 scopus 로고    scopus 로고
    • Ojima, I., Ed.; Wiley-VCH: New York
    • (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
    • (2000) Catalytic Asymmetric Synthesis
  • 12
    • 33745336054 scopus 로고
    • For example, the classic L-DOPA synthesis: Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 106
    • Knowles, W.S.1
  • 23
    • 0001390081 scopus 로고
    • For previous examples of asymmetric hydrogenation of electron-rich N-alkyl and N,N-dialkyl enamines, see: (a) Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5985
    • Lee, N.E.1    Buchwald, S.L.2
  • 28
    • 4043127711 scopus 로고    scopus 로고
    • note
    • It is postulated that the intramolecular hydrogen bond dictates this phenomenon. The (Z)-conformation of the substrates is confirmed by NMR (NOE).
  • 29
    • 4043062426 scopus 로고    scopus 로고
    • note
    • The effect of TFE in enamine ester hydrogenations can be mimicked by other acidic alcohols such as phenol derivatives.
  • 30
    • 4043122037 scopus 로고    scopus 로고
    • note
    • 2, we observed D-incorporation only in the β-position.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.