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Volumn 128, Issue 10, 2006, Pages 3112-3113

Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: An entry to functionalized γ-lactones

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; DICHLOROETHANE; DICHLOROMETHANE; GAMMA LACTONE DERIVATIVE; GOLD; PROPIOLIC ACID; TOLUENE; UNCLASSIFIED DRUG;

EID: 33644949668     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056857j     Document Type: Article
Times cited : (247)

References (53)
  • 5
    • 85043994028 scopus 로고    scopus 로고
    • Attanasi, O. A., Spinelli, D., Eds.; Springer: Berlin
    • (e) Bianchi, G.; Arcadi, A. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Springer: Berlin, 2004: Vol. 8, pp 82-119.
    • (2004) Targets in Heterocyclic Systems , vol.8 , pp. 82-119
    • Bianchi, G.1    Arcadi, A.2
  • 10
    • 25444517094 scopus 로고    scopus 로고
    • (c) Gagosz, F. Org. Lett. 2005, 7, 4129-4132.
    • (2005) Org. Lett. , vol.7 , pp. 4129-4132
    • Gagosz, F.1
  • 36
    • 2442685496 scopus 로고    scopus 로고
    • (b) For the addition of aryl to alkyne, see: Shi, S.; He, C. J. Org. Chem. 2004, 69, 3669-3671.
    • (2004) J. Org. Chem. , vol.69 , pp. 3669-3671
    • Shi, S.1    He, C.2
  • 40
  • 41
    • 33644953823 scopus 로고    scopus 로고
    • note
    • -1) was stirred under argon atmosphere at room temperature. After completion of the reaction, the mixture was filtered through a short pad of silica (EtOAc), and the solvents were evaporated under reduced pressure to give the corresponding lactone. No traces of methyl ketone were detected, even after reaction of the resulting lactone in the presence of AuCl and 10 equiv of water.
  • 42
    • 0348047259 scopus 로고    scopus 로고
    • The cyclizations of simpler alkynes, such as pent-4-ynoic acid, 2-phenyl-pent-4-ynoic acid, and 2-prop-2-ynylmalonic acid monomethyl ester, afforded a mixture of the exo-methylene lactones and the methyl ketones, presumably resulted from the formal Markovnikov-type hydration of the triple bond. For Au-catalyzed hydration reactions, see: (a) Schneider. S. K.; Hermann, W. A.; Herdtweck, E. Z. Anorg. Allg. Chem. 2003, 629, 2363-2370.
    • (2003) Z. Anorg. Allg. Chem. , vol.629 , pp. 2363-2370
    • Schneider, S.K.1    Hermann, W.A.2    Herdtweck, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.