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Volumn 40, Issue 7, 1999, Pages 1297-1300

Intramolecular carbocupration reaction of unactivated alkynes bearing a stabilized nucleophile: Application to the synthesis of iridoid monoterpenes

Author keywords

Alkynes; Cyclization; Iridoid monoterpenes; Vinyl copper

Indexed keywords

ALKYNE; IRIDOID; TERPENE DERIVATIVE;

EID: 0033547993     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02630-6     Document Type: Article
Times cited : (83)

References (29)
  • 1
    • 85119793503 scopus 로고
    • For leading references see: P. Knochel B. Trost I. Fleming Comprehensive Organic Synthesis Vol.4 1991 Pergamon Press New York 865 911
    • (1991) , pp. 865-911
    • Knochel, P.1
  • 2
    • 0003397783 scopus 로고    scopus 로고
    • Cross Coupling Reactions
    • I. Marek J.F. Normant Cross Coupling Reactions D. Diederich P. Stang 1998 VCH New York
    • (1998)
    • Marek, I.1    Normant, J.F.2
  • 11
    • 0031468875 scopus 로고    scopus 로고
    • N. Tsukada Y. Yamamoto A palladium-catalyzed cyclization of internal alkynes has recently been reported but is restricted to ε-alkynyl malononitriles: Angew. Chem. Int. Ed. Engl. 36 1997 2477 2480
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2477-2480
    • Tsukada, N.1    Yamamoto, Y.2
  • 20
    • 0041378607 scopus 로고
    • The cis-trans isomerisation of phenyl-substituted vinyllithium species has already been reported: D.H. Hunter D.J. Cram J. Am. Chem. Soc. 86 1964 5478 5490
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5478-5490
    • Hunter, D.H.1    Cram, D.J.2
  • 24
    • 0001139468 scopus 로고
    • An intermolecular Michael addition-intramolecular alkylation was termed ⪡ Michael-Initiated Ring Closure ⪢ by Little: R.D. Little J.R. Dawson Tetrahedron Lett. 1980 2609 2912
    • (1980) Tetrahedron Lett. , pp. 2609-2912
    • Little, R.D.1    Dawson, J.R.2
  • 25
    • 0028350815 scopus 로고
    • This order of reactivity is unusual since in the “one-pot” tandem alkylation-Michael sequence, malonic enolates are known to react according to a mechanism in which the alkylation step first takes place followed by the intramolecular Michael addition: D. Desmaele J-M. Louvet Tetrahedron Lett. 35 1994 2549 2552
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2549-2552
    • Desmaele, D.1    Louvet, J-M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.