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Volumn 53, Issue 8, 1997, Pages 2855-2870

Preparation of optically active α-Silylcarbonyl compounds using asymmetric alkylation of α-Silylacetic esters and asymmetric metal-carbene insertion into the Si-H bond.

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

EID: 0031584872     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00002-1     Document Type: Article
Times cited : (36)

References (55)
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    • 2. For other asymmetric access to α-silylcarbonyl compounds, see : (a) Enders, D.; Nakai, S. Helv. Chim. Acta, 1990, 73, 1833-1836;
    • (1990) Helv. Chim. Acta , vol.73 , pp. 1833-1836
    • Enders, D.1    Nakai, S.2
  • 24
    • 0001644203 scopus 로고
    • 5. 7a-c are commercially available. 7d was prepared by addition of the Grignard of 1-bromonaphtalene to (+)-camphor following a reported protocol : Somfai, P.; Tanner, D.; Olsson, T. Tetrahedron, 1985, 41, 5973-5980.
    • (1985) Tetrahedron , vol.41 , pp. 5973-5980
    • Somfai, P.1    Tanner, D.2    Olsson, T.3
  • 25
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    • and references cited therein
    • 6. Ye, T.; McKervey, M.A. Chem. Rev., 1994, 94, 1091-1160 and references cited therein.
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    • Ye, T.1    McKervey, M.A.2
  • 26
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    • and references cited therein
    • 7. Balwin, J.E.; Smith, R.A. J. Am. Chem. Soc., 1967, 89, 1886-1890 and references cited therein.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1886-1890
    • Balwin, J.E.1    Smith, R.A.2
  • 28
    • 0011436472 scopus 로고    scopus 로고
    • note
    • 11 might be invoked here. (equation presented)
  • 36
    • 0000177311 scopus 로고
    • 14. For a recent synthesis of α-diazoesters, see : Taber, D.F.; You, K.; Song, Y. J. Org. Chem., 1995, 60, 1093-1094.
    • (1995) J. Org. Chem. , vol.60 , pp. 1093-1094
    • Taber, D.F.1    You, K.2    Song, Y.3
  • 37
    • 0001068547 scopus 로고
    • 15. Chiral auxiliaries 16d-e are commercially available. 16b-c were prepared from (1S)-(+)-camphorquinone, following a reported procedure : Oppolzer, W.; Chapuis, C.; Dao, G.M.; Reichlin, D.; Godel, T. Tetrahedron Lett., 1982, 23, 4781-4784.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 4781-4784
    • Oppolzer, W.1    Chapuis, C.2    Dao, G.M.3    Reichlin, D.4    Godel, T.5
  • 39
    • 0001285938 scopus 로고
    • (b) Ort, O. Org. Synth., 1987, 65, 203-214.
    • (1987) Org. Synth. , vol.65 , pp. 203-214
    • Ort, O.1
  • 46
    • 0001782321 scopus 로고    scopus 로고
    • 21. For reviews on the use of the silicon group as a masked hydroxy group, see : (a) Fleming, I. Chemtracts, Org. Chem., 1996, 9, 1-64;
    • (1996) Chemtracts, Org. Chem. , vol.9 , pp. 1-64
    • Fleming, I.1
  • 47
    • 0030007621 scopus 로고    scopus 로고
    • 21a,b but was not performed in our case due to the low diastereosetectivity of the insertion process.
    • (1996) Tetrahedron , vol.52 , pp. 7599-7662
    • Jones, G.R.1    Landais, Y.2
  • 48
    • 0017136359 scopus 로고
    • 22. 24a is commercially available (Fluka). 24b : Mori, K. Tetrahedron, 1976, 32, 1101-1106; 24c : Bergstein, W.; Kleemann, A.; Martens, J. Synthesis, 1981, 76-78.
    • (1976) Tetrahedron , vol.32 , pp. 1101-1106
    • Mori, K.1
  • 49
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    • 22. 24a is commercially available (Fluka). 24b : Mori, K. Tetrahedron, 1976, 32, 1101-1106; 24c : Bergstein, W.; Kleemann, A.; Martens, J. Synthesis, 1981, 76-78.
    • (1981) Synthesis , pp. 76-78
    • Bergstein, W.1    Kleemann, A.2    Martens, J.3
  • 50
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    • 23. Acetals were prepared from die 1,2-diols in the presence of benzaldehyde and a catalytic amount of p-TsOH. The enantiomeric excesses were measured following Eliel's procedure : Eliel, E.L.; Ko, K.-Y. Tetrahedron Lett., 1983, 34, 3547-3550.
    • (1983) Tetrahedron Lett. , vol.34 , pp. 3547-3550
    • Eliel, E.L.1    Ko, K.-Y.2
  • 53
    • 0011437578 scopus 로고    scopus 로고
    • Reduction and C-Si bond oxidation of 27a-b gave diol 24a and 1-phenylethane-1,2-diol respectively.
    • 26. Reduction and C-Si bond oxidation of 27a-b gave diol 24a and 1-phenylethane-1,2-diol respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.