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Volumn 68, Issue 18, 2003, Pages 7041-7045

First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC CYCLE;

EID: 0041837372     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034752y     Document Type: Article
Times cited : (82)

References (63)
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    • (1999) Curr Med. Chem. , vol.6
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    • 0004286459 scopus 로고    scopus 로고
    • Oxford University Press: New York
    • (b) Procter, G. In Asymmetric Synthesis; Oxford University Press: New York, 1998.
    • (1998) Asymmetric Synthesis
    • Procter, G.1
  • 18
    • 0043153408 scopus 로고    scopus 로고
    • note
    • 16
  • 36
    • 0004252595 scopus 로고    scopus 로고
    • Grieco, P. A., Ed.; Blackie Academic and Professional: London
    • (b) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
    • (1998) Organic Synthesis in Water
  • 44
    • 0043153407 scopus 로고    scopus 로고
    • note
    • 22d,e
  • 45
    • 0042151474 scopus 로고    scopus 로고
    • note
    • 22a,b
  • 51
    • 0028204919 scopus 로고
    • 4 was used in methanol as reducing system: Rao, H. S. P.; Siva, P. Synth. Commun. 1994, 24, 549-555.
    • (1994) Synth. Commun. , vol.24 , pp. 549-555
    • Rao, H.S.P.1    Siva, P.2
  • 53
    • 0042151473 scopus 로고    scopus 로고
    • note
    • 4OH 0.1 M, the 2-hydroxy-3-aminohexanoic acid (9b) was isolated in 86% yield as a white crystalline solid. Recovered Cu(B) was dissolved in 20 mL of a water solution at pH 4.0, and the procedure was repeated. The catalyst was used four times without decreasing its efficiency. The structures of the products were confirmed by usual analyses; see Supporting Information.
  • 54
    • 0042652453 scopus 로고    scopus 로고
    • note
    • 6c,d
  • 57
    • 0042151472 scopus 로고    scopus 로고
    • note
    • 6c,d
  • 60
    • 0043153406 scopus 로고    scopus 로고
    • note
    • 20 = -11.7 (c = 0.52 in 1 N HCl).
  • 61
    • 0041650559 scopus 로고    scopus 로고
    • note
    • D = 29.2 (c = 0.25 1 N HCl). HPLC analysis on a chiral stationary phase, performed on the N-acetyl-methylester derivative, confirmed the enantiomeric purity of the starting epoxyalcohol 4 (Supporting Information).
  • 63
    • 0041650560 scopus 로고    scopus 로고
    • note
    • D = -5.4 (c = 0.51 in 1 N HCl). HPLC analysis on a chiral stationary phase, performed on the N-acetyl-methylester derivative, confirmed the enantiomeric purity of the starting epoxyalcohol 5 (Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.