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Volumn , Issue 7, 2000, Pages 935-940

The reaction of chromium alkenyl carbene complexes with alkenyl oxazolines: A diastereoselective [3+2] annulation route to cyclopentanones

Author keywords

Carbene complexes; Chromium; Stereoselective

Indexed keywords

ALKENE; CARBENE; CYCLOPENTENONE DERIVATIVE;

EID: 0033935931     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6306     Document Type: Article
Times cited : (16)

References (26)
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    • The cyclopropanation of electron-rich alkenes, e.g. enamines, takes place much more sluggishly, see: Wulff, W. D.; Yang, D. C.; Murray, C. K. Pure Appl. Chem. 1988, 60, 137.
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    • Wulff, W.D.1    Yang, D.C.2    Murray, C.K.3
  • 14
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    • Cyclopropanes derived from pentacarbonyl phenyl(methoxy)carbene chromium complex and methyl penta-2,4-dienoate esters rearrange slowly at 160-190 °C to give mixtures of various diastereoisomers. See, Buchert, M.; Reissig, H.-U. Liebigs Ann. Chem. 1996, 2007.
    • (1996) Liebigs Ann. Chem. , pp. 2007
    • Buchert, M.1    Reissig, H.-U.2
  • 15
    • 0342907536 scopus 로고    scopus 로고
    • For an example of charge-induced vinylcyclopropane-cyclopentene rearrangement, see Ref. 10
    • For an example of charge-induced vinylcyclopropane-cyclopentene rearrangement, see Ref. 10.
  • 18
    • 0001373505 scopus 로고
    • Rearrangement of vinylcyclopropanes and related systems
    • Trost, B.M.; Fleming, I. Eds.; Pergamon: New York, Chapter 8.1
    • Hudlicky, T.; Reed, J. W. Rearrangement of Vinylcyclopropanes and Related Systems. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 8.1, pp 899-970.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899-970
    • Hudlicky, T.1    Reed, J.W.2
  • 19
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    • For an elegant syntesis of (±)-Prostaglandin E2 from a dienyl carbene complex and an enolether, see: Murray, C. K.; Yang, D. C.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 5660.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5660
    • Murray, C.K.1    Yang, D.C.2    Wulff, W.D.3
  • 20
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    • For instance, ethyl 2-ethenyl-2-methoxycyclopropane-carboxylate rearranges at 160 °C in the presence of copper catalysts. See: Doyle, M.P.; Van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 5917
    • Doyle, M.P.1    Van Leusen, D.2
  • 21
    • 0000896139 scopus 로고
    • The energy barriers for rotation about carbon-carbon bonds in alkyl-substituted allyl cations have been estimated to be less than 25 Kcal/mol: Bollinger, J.M.; Brinich, J.M.; Olah, G.A, J. Am. Chem. Soc. 1970, 92, 4025.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 4025
    • Bollinger, J.M.1    Brinich, J.M.2    Olah, G.A.3
  • 23
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    • Transition metal mediated cycloadditions
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, Chapter 3.2
    • Chan, D. M. T. Transition Metal Mediated Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 3.2, pp 308-312.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 308-312
    • Chan, D.M.T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.