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Volumn 350, Issue 6, 2008, Pages 791-796

Organocatalytic anti-Mannich reactions with dihydroxyacetone and acyclic dihydroxyacetone derivatives: A facile route to amino sugars

Author keywords

Acyclic dihydroxyacetone derivatives; Anti Mannich reaction; Dihydroxyacetone; Primary amine containing amino acids

Indexed keywords


EID: 50649103777     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800069     Document Type: Article
Times cited : (32)

References (53)
  • 1
    • 53849090444 scopus 로고    scopus 로고
    • Ed, C.-H. Wong, Wiley-VCH, Weinheim, chap. 26.3;
    • a) Carbohydrate Based Drug Discovery, (Ed.: C.-H. Wong), Wiley-VCH, Weinheim, 2003, chap. 26.3;
    • (2003) Carbohydrate Based Drug Discovery
  • 3
    • 53849112090 scopus 로고    scopus 로고
    • Ed, C.-H. Wong, Wiley-VCH, Weinheim, chap. 24;
    • c) Carbohydrate Based Drug Discovery, (Ed.: C.-H. Wong), Wiley-VCH, Weinheim, 2003, chap. 24;
    • (2003) Carbohydrate Based Drug Discovery
  • 11
    • 0028338631 scopus 로고
    • and references cited therein; For selected references, see: a
    • For selected references, see: a) E. W. Baxter, A. B. Reitz, J. Org. Chem. 1994, 59, 3175, and references cited therein;
    • (1994) J. Org. Chem , vol.59 , pp. 3175
    • Baxter, E.W.1    Reitz, A.B.2
  • 13
    • 0031907833 scopus 로고    scopus 로고
    • For selected references, see: a
    • For selected references, see: a) A. I. Meyers, D. A. Price, Chirality, 1998, 10, 88;
    • (1998) Chirality , vol.10 , pp. 88
    • Meyers, A.I.1    Price, D.A.2
  • 42
    • 37649024285 scopus 로고    scopus 로고
    • [4c,d,7a] Córdova et al. published related results; P. Dziedzic, I. Ibrahem, A. H. Córdova, Tetrahedron Lett. 2008, 49, 803.
    • [4c,d,7a] Córdova et al. published related results; P. Dziedzic, I. Ibrahem, A. H. Córdova, Tetrahedron Lett. 2008, 49, 803.
  • 46
    • 28444445588 scopus 로고    scopus 로고
    • For other anti-Mannich reactions based on enamine catalysis, see: d T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408;
    • For other anti-Mannich reactions based on enamine catalysis, see: d) T. Kano, Y. Yamaguchi, O. Tokuda, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 16408;
  • 49
    • 53849115904 scopus 로고    scopus 로고
    • H-tetrazole were the best choices considering the reaction rate, yield, and selectivity (data not shown)
    • Solvent and additive screening at room temperature showed that NMP and 5-methyl-1, as an acid co-catalyst
    • Solvent and additive screening at room temperature showed that NMP and 5-methyl-1H-tetrazole were the best choices considering the reaction rate, yield, and selectivity (data not shown). 5-Methyl-1H-tetrazole acts as an acid co-catalyst.
    • 5-Methyl-1H-tetrazole acts
  • 50
    • 53849117281 scopus 로고    scopus 로고
    • [5]
    • [5]
  • 52
    • 53849087657 scopus 로고    scopus 로고
    • [8e]
    • [8e]
  • 53
    • 53849148045 scopus 로고    scopus 로고
    • Poor enantioselectivity was observed in the β-proline catalyzed Mannich reaction with Bn-protected DHA and ethyl glyoxylate imine; dr 1.4:1 (anti:syn) and 45% ee anti, see ref.[8c
    • [8c]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.