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Volumn 53, Issue 30, 1997, Pages 10271-10280

Asymmetric aldol addition of aldehydes to a difluoroketene silyl acetal catalyzed by chiral Lewis acids

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

EID: 0030873311     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00683-2     Document Type: Article
Times cited : (85)

References (36)
  • 12
    • 0002877308 scopus 로고
    • Synthesis and biochemical applications of fluorine-containing peptides and proteins
    • Kukhar', V.P.; Soloshonok, V.A. Eds.; John Wiley and Sons, Inc.: New York
    • c) For a review see: Kirk, K.L. Synthesis and Biochemical Applications of Fluorine-containing Peptides and Proteins. In Fluorine-containing Amino Acids; Kukhar', V.P.; Soloshonok, V.A. Eds.; John Wiley and Sons, Inc.: New York, 1995; pp. 343-401.
    • (1995) Fluorine-containing Amino Acids , pp. 343-401
    • Kirk, K.L.1
  • 19
    • 0343195635 scopus 로고    scopus 로고
    • note
    • The difluoroketene silyl acetal 1 is considerably stable and can be stored at -20°C over several months.
  • 20
    • 0003788192 scopus 로고
    • and references cited therein
    • The CAB catalyst developed by Yamamoto at al. (Furuta, K.; Maruyama, T.; Yamamoto, H. Synlett, 1991, 439-440 and references cited therein) and the BINOL-derived titanium complex of Mikami et al. (Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078 and references cited therein) were not effective for enamioselectivity.
    • (1991) Synlett , pp. 439-440
    • Furuta, K.1    Maruyama, T.2    Yamamoto, H.3
  • 21
    • 0001087242 scopus 로고
    • and references cited therein were not effective for enamioselectivity
    • The CAB catalyst developed by Yamamoto at al. (Furuta, K.; Maruyama, T.; Yamamoto, H. Synlett, 1991, 439-440 and references cited therein) and the BINOL-derived titanium complex of Mikami et al. (Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078 and references cited therein) were not effective for enamioselectivity.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4077-4078
    • Mikami, K.1    Matsukawa, S.2
  • 22
    • 0001015876 scopus 로고
    • 3·THF and p-toluenesulfonamide of the corresponding amino acid in nitroethane at 45°C for 1 h. See: a) Parmee, E.R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365-9366.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9365-9366
    • Parmee, E.R.1    Tempkin, O.2    Masamune, S.3
  • 27
    • 33745775152 scopus 로고
    • The aldol reaction of enoxysilacyclobutanes was reported to proceed through cyclic transition states in the absence of Lewis acids. See: a) Myers, A.G.; Kephart, S.E.; Chen, H. J. Am. Chem. Soc. 1992, 114, 7922-7923.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7922-7923
    • Myers, A.G.1    Kephart, S.E.2    Chen, H.3
  • 30
    • 0001087242 scopus 로고
    • Mikami et al. suggested the silatropic ene mechanism for the asymmetric catalysis of aldol-type reactions with ketene silyl acetals. See: a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4077-4078
    • Mikami, K.1    Matsukawa, S.2
  • 32
    • 0029860701 scopus 로고    scopus 로고
    • The aldol reaction catalyzed by a bidentate Lewis acid was reported by Maruoka et al. See: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307-11308.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11307-11308
    • Ooi, T.1    Takahashi, M.2    Maruoka, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.