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Volumn 40, Issue 13, 1999, Pages 2581-2584

Intramolecular ketyl-olefin cyclization mediated by magnesium metal

Author keywords

Intramolecular cyclization; Ketyl radical; Magnesium

Indexed keywords

ACETYLENE; ALKENE; CARBON; KETONE; MAGNESIUM;

EID: 0033605884     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00252-X     Document Type: Article
Times cited : (6)

References (43)
  • 2
    • 0000315424 scopus 로고
    • Trost, B. M. and Fleming, I. Eds;Pergamon Press; Oxford
    • (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I. Eds;Pergamon Press; Oxford, 1991; vol. 4; pp 779-831.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 779-831
    • Curran, D.P.1
  • 30
    • 0000104215 scopus 로고
    • Trost, B. M.; Fleming, I., Eds; Pergamon Press: Oxford, Great Britain, Chapter 9
    • (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 251
    • Molander, G.A.1
  • 37
    • 0013579078 scopus 로고    scopus 로고
    • Magnesium in methanol promotes reductive cyclization of ketones tethered to olefin substituted with electron withdrawing ester or nitrile group, however, it is uncertain that whether the reaction proceed through addition of ketyl to olefin or allyl anion to carbonyl group (see ref 8a)
    • Magnesium in methanol promotes reductive cyclization of ketones tethered to olefin substituted with electron withdrawing ester or nitrile group, however, it is uncertain that whether the reaction proceed through addition of ketyl to olefin or allyl anion to carbonyl group (see ref 8a).
  • 38
    • 0013601797 scopus 로고    scopus 로고
    • The structure and relative stereochemistry of It as well as other products were elucidated by 2-D COSY and 1-D NOE difference spectra
    • The structure and relative stereochemistry of It as well as other products were elucidated by 2-D COSY and 1-D NOE difference spectra.
  • 43
    • 0013628977 scopus 로고    scopus 로고
    • note
    • The starting ketone 5 was synthesized in 99% yield (ZIE; 1/1) by the reaction of ethyl 2-methylacetoacetate with 1.1 equiv 90% acrolein in diethyl ether at room temperature followed by Wittig reaction without further purification of the intermediate aldehyde.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.