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Volumn 55, Issue 13, 1999, Pages 4029-4042

Thermodynamic vs. kinetic control in the stereoselective intramolecular conjugate addition of amide enolates leading to chiral trans-3,4- disubstituted pyrrolidin-2-ones

Author keywords

Cyclisation; Michael reaction; Pyrrolidinones; Stereoselection

Indexed keywords

AMIDE; PYRROLIDIN 2 ONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033605898     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00091-5     Document Type: Article
Times cited : (17)

References (39)
  • 9
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    • A method leading to 1,3,4-trisubstituted pyrrolidin-2-ones proceeding via palladium-catalysed intramolecular allylation has been recently reported: Giambastiani, G.; Pacini, B.; Porcelloni, M.; Poli, G. J. Org. Chem., 1998, 63, 804-807.
    • (1998) J. Org. Chem. , vol.63 , pp. 804-807
    • Giambastiani, G.1    Pacini, B.2    Porcelloni, M.3    Poli, G.4
  • 20
    • 0013616862 scopus 로고
    • Atta-ur-Rahman, Ed., Elsevier Science: Amsterdam
    • a) Georg, G.I. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed., Elsevier Science: Amsterdam, 1989, vol. 4, p. 431-456.
    • (1989) Studies in Natural Product Chemistry , vol.4 , pp. 431-456
    • Georg, G.I.1
  • 25
    • 0003573894 scopus 로고
    • Pergamon Press, Oxford
    • Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1992. For some recent examples concerning stereoselective intramolecular coniugate additions leading to pyrrolidine or piperidine ring formation. see also:
    • (1992) Conjugate Addition Reactions in Organic Synthesis
    • Perlmutter, P.1
  • 30
    • 0013589843 scopus 로고    scopus 로고
    • note
    • A R,S mixture of the corresponding azetidinone can be easily converted into the 1β-methyl derivative, exclusively (ref.8a).
  • 32
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    • and subsequent versions, e.g. MM2-87, MM2-89, MM2-91
    • b) Allinger, N.L. J. Am. Chem. Soc., 1977, 99, 8127-8134, and subsequent versions, e.g. MM2-87, MM2-89, MM2-91.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127-8134
    • Allinger, N.L.1
  • 34
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    • The relative energies of the two diastereomers were calculated by using the AM1 Hamiltonian. As references see: Dewar, M.J.S.; Zoebisch, E.G. Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc., 1985, 107, 3902-3909. The program is enclosed in Hyperchem package, release 5.01, available from Hypercube, Gainesville, Florida, U.S.A.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 35
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    • The reversibility of the conjugate addition allows for the formation of the lower energy product. See, for example: Chan, S.; Braish, T.F. Tetrahedron, 1994, 50, 9943-9950.
    • (1994) Tetrahedron , vol.50 , pp. 9943-9950
    • Chan, S.1    Braish, T.F.2
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    • note
    • -1, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.