메뉴 건너뛰기




Volumn 125, Issue 24, 2003, Pages 7291-7300

Michael addition of stannyl ketone enolate to α,β-unsaturated esters catalyzed by tetrabutylammonium bromide and an ab initio theoretical study of the reaction course

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ADDITION REACTIONS; BROMINE COMPOUNDS; CATALYSIS; ESTERS; NEGATIVE IONS;

EID: 0038451211     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028853+     Document Type: Article
Times cited : (47)

References (39)
  • 1
    • 0004015228 scopus 로고
    • Pergamon Press: Oxford, U.K.
    • Comprehensive Organic Syntheses; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 4.
    • (1991) Comprehensive Organic Syntheses , vol.4
  • 2
    • 0001723738 scopus 로고
    • Simple examples using lithium enolate under thermal conditions for types A-C: (a) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157-172. (b) Yamaguchi, M.; Tsukamoto, M.; Hirao, I. Chem. Lett. 1984, 375-376.
    • (1990) J. Org. Chem. , vol.55 , pp. 157-172
    • Oare, D.A.1    Heathcock, C.H.2
  • 3
    • 0001723738 scopus 로고
    • Simple examples using lithium enolate under thermal conditions for types A-C: (a) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157-172. (b) Yamaguchi, M.; Tsukamoto, M.; Hirao, I. Chem. Lett. 1984, 375-376.
    • (1984) Chem. Lett. , pp. 375-376
    • Yamaguchi, M.1    Tsukamoto, M.2    Hirao, I.3
  • 4
    • 33947338175 scopus 로고
    • The classical example using a strong base for the addition of cycloalkanone enolate to enoates. House, H. O.; Roelofs, W. L.; Trost, B. M. J. Org. Chem. 1966, 31, 646-655.
    • (1966) J. Org. Chem. , vol.31 , pp. 646-655
    • House, H.O.1    Roelofs, W.L.2    Trost, B.M.3
  • 5
    • 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. (b) Lee, R. A. Tetrahedron Lett. 1973, 3333-3336.
    • (1957) J. Org. Chem. , vol.22 , pp. 1268-1269
    • Miller, J.J.1    De Benneville, P.L.2
  • 6
    • 0001258911 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. (b) Lee, R. A. Tetrahedron Lett. 1973, 3333-3336.
    • (1973) Tetrahedron Lett. , pp. 3333-3336
    • Lee, R.A.1
  • 8
    • 0038422082 scopus 로고    scopus 로고
    • note
    • As expected from this assumption, reaction type A including transformation from ester enolate to ketone enolate shows the largest stabilization.
  • 17
    • 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
  • 31
    • 0038760024 scopus 로고    scopus 로고
    • note
    • The potential energy profile around the transition state between E and G is too flat and includes several local energy maximums, whose levels are lower than that of D. The structure F has the highest energy level among them between E and G. The difference between the uncatalyzed and catalyzed reactions can be discussed by comparing A and D.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.