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Volumn 46, Issue 19, 2005, Pages 3363-3367

Amino acid catalyzed direct enantioselective formation of carbohydrates: One-step de novo synthesis of ketoses

Author keywords

Amino acids; Asymmetric synthesis; Biomimetic; Carbohydrates; Catalysis

Indexed keywords

ALDEHYDE; AMINO ACID; AMINOSUGAR; CARBOHYDRATE; DEOXYSUGAR; DIHYDROXYACETONE PHOSPHATE; FRUCTOSE; IMINE; KETOSE; PISCOSE; RIBULOSE; TAGATOSE; UNCLASSIFIED DRUG; WATER;

EID: 17244373834     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.084     Document Type: Article
Times cited : (131)

References (86)
  • 47
    • 17244378815 scopus 로고    scopus 로고
    • For an excellent review on the use of protected dihydroxy acetones in synthesis see: D. Enders, M. Voith, and A. Lenzen Angew. Chem., Int. Ed. 44 2005 1330 and references cited therein
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1330
    • Enders, D.1    Voith, M.2    Lenzen, A.3
  • 54
    • 15444380834 scopus 로고    scopus 로고
    • During the preparation of this manuscript an excellent manuscript by Enders and Grondal appeared that described a similar amino acid catalyzed one-step carbohydrate synthesis, which took six days in DMF D. Enders, and C. Grondal Angew. Chem., Int. Ed. 44 2005 1210
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1210
    • Enders, D.1    Grondal, C.2
  • 56
    • 4544382328 scopus 로고    scopus 로고
    • This beneficial effect of water has been observed in other amino acid catalyzed C-C bond-forming reactions. See: A.I. Nyberg, A. Usano, and P. Pihko Synlett 2004 1891
    • (2004) Synlett , pp. 1891
    • Nyberg, A.I.1    Usano, A.2    Pihko, P.3
  • 62
    • 85030794663 scopus 로고    scopus 로고
    • note
    • 4, filtered and concentrated. The pure protected sugars 2 were obtained by silica gel column chromatography (toluene/EtOAc mixtures)
  • 63
    • 85030797737 scopus 로고    scopus 로고
    • note
    • +: calcd 303.1208)
  • 64
    • 85030796187 scopus 로고    scopus 로고
    • note
    • +: calcd 283.2734)
  • 65
    • 0034721440 scopus 로고    scopus 로고
    • Amino acid catalyzed Mannich reactions: Ketones as donors see: B. List J. Am. Chem. Soc. 122 2000 9336
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336
    • List, B.1
  • 81
    • 85030793421 scopus 로고    scopus 로고
    • note
    • 4, filtered and concentrated. The pure protected sugars 3 were obtained by silica gel column chromatography (toluene/EtOAc mixtures)
  • 82
    • 85030800081 scopus 로고    scopus 로고
    • note
    • +: calcd 408.1787)
  • 83
    • 85030800723 scopus 로고    scopus 로고
    • note
    • +: calcd 388.1736)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.