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Volumn 349, Issue 14-15, 2007, Pages 2301-2306

Intramolecular aza-anti-Michael addition of an amide anion to enones: A regiospecific approach to tetramic acid derivatives

Author keywords

Amide anion; Anti Michael addition; Enones; Tetramic acids

Indexed keywords


EID: 35948940824     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600542     Document Type: Article
Times cited : (52)

References (45)
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    • For a review, see: a
    • For a review, see: a) E. Lewandowska, Tetrahedron 2007, 63, 1101-1112;
    • (2007) Tetrahedron , vol.63 , pp. 1101-1112
    • Lewandowska, E.1
  • 9
    • 0025300797 scopus 로고    scopus 로고
    • E. Patonay-Péli, G. Litkei, T. Patonay, Synthesis 1990, 511-514. If no azide group is present at the α-position of enones, an exclusive intramolecular Michael ad.dition will occur instead of the anti-Michael addition, please see:
    • a) E. Patonay-Péli, G. Litkei, T. Patonay, Synthesis 1990, 511-514. If no azide group is present at the α-position of enones, an exclusive intramolecular Michael ad.dition will occur instead of the anti-Michael addition, please see:
  • 22
    • 0001246453 scopus 로고
    • For selected recent examples, see: 2001
    • b) B. J. L. Royles, Chem. Rev. 1995, 95, 1981-2001. For selected recent examples, see:
    • (1981) Chem. Rev , vol.95
    • Royles, B.J.L.1
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    • 30744435706 scopus 로고
    • Further Perspectives in Organic Chemistry
    • Elsevier, Amsterdam
    • b) J. E. Baldwin, Further Perspectives in Organic Chemistry, A Ciba Foundation Symposium, Elsevier, Amsterdam, 1978, p 85.
    • (1978) A Ciba Foundation Symposium , pp. 85
    • Baldwin, J.E.1
  • 35
    • 11844279065 scopus 로고    scopus 로고
    • For some examples of intramolecular aza-Michael addition, see : a G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E. Torregiani, J. Org. Chem. 2005, 70, 169-174;
    • For some examples of intramolecular aza-Michael addition, see : a) G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E. Torregiani, J. Org. Chem. 2005, 70, 169-174;
  • 39
    • 35948990177 scopus 로고    scopus 로고
    • In one case where the enone substrate 6m has a β-4methoxyphenyl, a complex mixture product was formed under the identical conditions as described in Scheme 1, from which an aza-Michael adduct 6m-i was separated and confirmed by subsequent reduction and elimination reactions.
    • In one case where the enone substrate 6m has a β-4methoxyphenyl, a complex mixture product was formed under the identical conditions as described in Scheme 1, from which an aza-Michael adduct 6m-i was separated and confirmed by subsequent reduction and elimination reactions.
  • 41
    • 35948930348 scopus 로고    scopus 로고
    • For the calculation details, please see Supporting Information
    • For the calculation details, please see Supporting Information.
  • 44
    • 0001617183 scopus 로고    scopus 로고
    • For a general discussion of the importance of the proximity of the reacting centers in intramolecular reactions, see: F. M. Menger, Acc Chem. Res. 1985, 18, 128-134;
    • For a general discussion of the importance of the proximity of the reacting centers in intramolecular reactions, see: F. M. Menger, Acc Chem. Res. 1985, 18, 128-134;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.