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Volumn 8, Issue 1, 1997, Pages 109-131

Asymmetric nitrone-vinyl sulfoxide cycloadditions

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINOALCOHOL; HALOSALINE; HYGROLINE; PELLETIERINE; PIPERIDINE DERIVATIVE; SEDRIDINE; UNCLASSIFIED DRUG;

EID: 0031031948     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00480-6     Document Type: Article
Times cited : (64)

References (48)
  • 1
    • 11944251609 scopus 로고
    • For general reviews see: (a) Carreño, M. C.; Chem. Rev. 1995, 95, 1717-1760;
    • (1995) Chem. Rev. , vol.95 , pp. 1717-1760
    • Carreño, M.C.1
  • 3
    • 0002335594 scopus 로고
    • Patai, S; Rappoport, Z.; Stirling, C. J. M. Eds.; John Wiley, New York
    • (c) Posner, G. H. In The Chemistry of Sulphones and Sulphoxides; Patai, S; Rappoport, Z.; Stirling, C. J. M. Eds.; John Wiley, New York 1988, pp. 823-846.
    • (1988) The Chemistry of Sulphones and Sulphoxides , pp. 823-846
    • Posner, G.H.1
  • 17
    • 24444446563 scopus 로고
    • EtOH was found to inhibit the competitive nitrone dimerization: Gössinger, E. Monatsh. Chem. 1982, 113, 339-354.
    • (1982) Monatsh. Chem. , vol.113 , pp. 339-354
    • Gössinger, E.1
  • 19
    • 0000677232 scopus 로고
    • Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
    • (1993) Chem. Rev. , vol.93 , pp. 2023-2035
    • Li, C.-J.1
  • 24
    • 33947476818 scopus 로고
    • For a review on Raney Nickel-promoted desulfurization see: Hauptmann, H.; Walker, W. F. Chem. Rev. 1962, 62, 347-404.
    • (1962) Chem. Rev. , vol.62 , pp. 347-404
    • Hauptmann, H.1    Walker, W.F.2
  • 27
    • 1542735933 scopus 로고    scopus 로고
    • Treatment of (±)-sedridine (±)-9a with an excess of Ni/Al alloy in alkaline medium (desulfurization conditions) yielded an 1/1 mixture of C8-epimeric alcohols (±)-sedridine (±)-9a and (±)-allosedridine (±)-23a. For related cases see ref. 3b and Butlin, R. J.; Linney, I. D.; Mahon, M. F.; Tye, H.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 95-105.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 95-105
    • Butlin, R.J.1    Linney, I.D.2    Mahon, M.F.3    Tye, H.4    Wills, M.5
  • 33
    • 0342527237 scopus 로고    scopus 로고
    • unpublished results
    • D+30.9 (MeOH; c 2.0)} by N-acylation and Swern oxidation. Louis, C.; Hootelé, C. unpublished results.
    • Louis, C.1    Hootelé, C.2
  • 34
    • 0003910514 scopus 로고
    • Marcel Dekker, New York
    • W6 Raney Nickel was prepared according to: Augustine, R. L. Catalytic Hydrogenation; Marcel Dekker, New York, 1965, pp. 147-148.
    • (1965) Catalytic Hydrogenation , pp. 147-148
    • Augustine, R.L.1
  • 40
    • 0343832513 scopus 로고    scopus 로고
    • note
    • D+156 (pyridine; c 1.3)}. The discrepancy observed between the values reported for the synthetic and the resolved samples can be ascribed to the low precision of the measurements in this case (±10%).
  • 45
    • 4243516107 scopus 로고
    • X-Ray diffraction analysis of (-)-(Z)-β-styryl p-tolyl sulfoxide 7d revealed that, in the solid state, the sulfur lone pair and the C-C double bond are syn coplanar: Declercq, J. P.; Feneau-Dupont, J.; Louis, C.; Hootelé, C. Acta Cryst. C 1994, 50, 1980-1981.
    • (1994) Acta Cryst. C , vol.50 , pp. 1980-1981
    • Declercq, J.P.1    Feneau-Dupont, J.2    Louis, C.3    Hootelé, C.4
  • 48
    • 0342527234 scopus 로고    scopus 로고
    • in press
    • In this series, optical rotations measured for amino alcohols 23 in ethanol are much lower than those of their epimers 9: Mill, S.; Durant, A.; Hootelé, C. Liebigs Ann. Chem. in press. Therefore we assume that the sign of the specific rotation measured for a mixture of 9 (major) and 23 (minor) refers to 9.
    • Liebigs Ann. Chem.
    • Mill, S.1    Durant, A.2    Hootelé, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.