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Volumn 64, Issue 7, 1999, Pages 2180-2181

The first michael addition of metal ketone enolates to α,β- unsaturated esters under catalytic conditions: Tin enolate with a catalytic amount of tetrabutylammonium bromide

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; KETONE; METAL DERIVATIVE; TETRABUTYLAMMONIUM; TIN DERIVATIVE;

EID: 0033515607     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990062b     Document Type: Article
Times cited : (26)

References (40)
  • 12
    • 0344246017 scopus 로고    scopus 로고
    • note
    • We should note the difference in the reactivities between ketone enolates and ester enolates, though they are often treated without distinction.
  • 14
    • 0008520710 scopus 로고
    • The subsequent step such as cyclization after Michael addition contributes to the stabilization of the product system: (a) Miller, J. J.; de Benneville, P. L. J. Org. Chem. 1957, 22, 1268-1269.
    • (1957) J. Org. Chem. , vol.22 , pp. 1268-1269
    • Miller, J.J.1    De Benneville, P.L.2
  • 26
    • 84987319931 scopus 로고
    • and references therein
    • (b) Enders, D.; Karl, W. SYNLETT 1992, 895-897 and references therein.
    • (1992) SYNLETT , pp. 895-897
    • Enders, D.1    Karl, W.2
  • 27
    • 0001960224 scopus 로고
    • Organotin enolates exist as equilibrium mixtures of keto- and/or enol forms; 1e and 1c exclusively exist in keto and enol forms, respectively: Pereyre, M.; Bellegarde, B.; Mendelsohn, J.; Valade, J. J. Organomet. Chem. 1968, 11, 97-110.
    • (1968) J. Organomet. Chem. , vol.11 , pp. 97-110
    • Pereyre, M.1    Bellegarde, B.2    Mendelsohn, J.3    Valade, J.4
  • 28
    • 0002476625 scopus 로고
    • Enol forms generally show higher reactivity than keto forms: Kobayashi, K.; Kawanisi, M.; Hitomi, T.; Kozima, S. Chem. Lett. 1983, 851-854. The low yield in the reaction of keto form enolate was probably caused by thermodynamic factors.
    • (1983) Chem. Lett. , pp. 851-854
    • Kobayashi, K.1    Kawanisi, M.2    Hitomi, T.3    Kozima, S.4
  • 30
    • 0002729236 scopus 로고
    • For the organotin ester enolates, the equilibrium between O-stannylated and C-stannylated forms generally lies to the C-stannylated species above O°C. Shimada, E.; Inomata, K.; Mukaiyama, T. Chem. Lett. 1974, 689-690.
    • (1974) Chem. Lett. , pp. 689-690
    • Shimada, E.1    Inomata, K.2    Mukaiyama, T.3
  • 37
    • 0001383034 scopus 로고
    • The fluoride anion catalyzed-Michael addition of ketene silyl acetals to enones has been reported, showing a similar highly coordinated silicon species. RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083-2089.
    • (1984) J. Org. Chem. , vol.49 , pp. 2083-2089
    • Rajanbabu, T.V.1
  • 40
    • 0345108344 scopus 로고    scopus 로고
    • note
    • The coordination by bromide anion suppresses the carbonyl addition of the tin enolate (ref 20a).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.