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Volumn 2, Issue 18, 2000, Pages 2769-2772

New synthetic technology for efficient construction of α-hydroxy-β-amino amides via the passerini reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; BESTATIN; DRUG DERIVATIVE; FLUORENE DERIVATIVE; LEUCINE; N(ALPHA) FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS; N(ALPHA)-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS; OXOACID; PROTEINASE INHIBITOR;

EID: 0034618307     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061485     Document Type: Article
Times cited : (127)

References (51)
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    • note
    • Dedicated to the memory of Joseph E. Semple.
  • 2
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    • Abstracts of papers
    • San Francisco, CA, March 26-30, American Chemical Society: Washington, DC, 2000; ORGN.667
    • Semple, J. E. Abstracts of Papers, 219th National Meeting of the American Chemical Society, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC, 2000; ORGN.667.
    • (2000) 219th National Meeting of the American Chemical Society
    • Semple, J.E.1
  • 15
    • 0033588064 scopus 로고    scopus 로고
    • and references therein
    • For an excellent compilation of the leading stereospecific and asymmetric approaches to α-hydroxy-β-amino acids and amides, see: Wasserman, H. H.; Xia, M.; Jorgensen, M. R.; Curtis, E. A. Tetrahedron Lett 1999, 40, 6163 and references therein.
    • (1999) Tetrahedron Lett , vol.40 , pp. 6163
    • Wasserman, H.H.1    Xia, M.2    Jorgensen, M.R.3    Curtis, E.A.4
  • 31
    • 0041050027 scopus 로고
    • Ugi, I., Ed.; Academic Press: New York
    • (c) Ugi, I. in Isonitrile Chemistry; Ugi, I., Ed.; Academic Press: New York, 1971, Chapter 7.
    • (1971) Isonitrile Chemistry , pp. 7
    • Ugi, I.1
  • 35
    • 84981758187 scopus 로고
    • Aqueous mineral acid-catalyzed versions
    • (a) Aqueous mineral acid-catalyzed versions: Hagedorn, I.; Eholzer, U. Chem. Ber. 1965, 98, 936.
    • (1965) Chem. Ber. , vol.98 , pp. 936
    • Hagedorn, I.1    Eholzer, U.2
  • 36
    • 84982336930 scopus 로고
    • 3 to directly produce α-hydroxyamides
    • 3 to directly produce α-hydroxyamides: Muller, E.; Zeeh, B. Liebigs Ann. Chem. 1966, 696, 72.
    • (1966) Liebigs Ann. Chem. , vol.696 , pp. 72
    • Muller, E.1    Zeeh, B.2
  • 41
    • 0019809851 scopus 로고
    • Passerini reaction of simple aldehydes and ketones with TFA and pyridine: Lumma, W. J. Org. Chem. 1981, 46, 3668.
    • (1981) J. Org. Chem. , vol.46 , pp. 3668
    • Lumma, W.1
  • 47
    • 0040455986 scopus 로고    scopus 로고
    • note
    • 4, filtered, and concentrated. The crude product was either recrystallized or purified by flash column chromatography on silica gel using ethyl acetate/hexane or dichloromethane/methanol gradient systems. Pure products were obtained as either nearly colorless solids or as colorless to pale yellow viscous oils.
  • 49
    • 85087227548 scopus 로고    scopus 로고
    • note
    • R = 14.0 min (Chiracel AD column: 2-propanol, hexane 10-30% gradient; 0.5 mL/min flow rate).
  • 51
    • 0034616838 scopus 로고    scopus 로고
    • After this paper was submitted, we became aware of a recent related publication: Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985.
    • (2000) Chem. Commun. , pp. 985
    • Banfi, L.1    Guanti, G.2    Riva, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.