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Volumn 69, Issue 9, 2004, Pages 3102-3111

Palladium(II)-Catalyzed Intramolecular 1,4-Oxyacyloxylation of Conjugated Dienes. A Stereocontrolled Route to Fused Six-Membered Lactones and Pyrans

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; LITHIUM COMPOUNDS; OXIDATION; PALLADIUM; SOLVENTS; STEREOCHEMISTRY;

EID: 2142698607     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0357667     Document Type: Article
Times cited : (21)

References (55)
  • 3
    • 0001546711 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For a review on reactions of metal-activated alkenes with heteroatom nucleophiles, see: Hegedus, L. S. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; pp 551-583.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 551-583
    • Hegedus, L.S.1
  • 15
    • 0003321649 scopus 로고
    • Abel, E. W., Stone, G. A., Wilkinson, G., Eds. (Hegedus, L. S., Vol. Ed.); Pergamon: New York
    • (b) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, G. A., Wilkinson, G., Eds. (Hegedus, L. S., Vol. Ed.); Pergamon: New York, 1995; Vol. 12, pp 797-904.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 797-904
    • Harrington, P.J.1
  • 29
    • 2142735713 scopus 로고    scopus 로고
    • note
    • The increased flexibility of the acid-functionalized tether rendered the lactonization reaction too slow compared to the intermolecular reaction.
  • 39
    • 2142741291 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra.
  • 40
    • 2142839327 scopus 로고    scopus 로고
    • note
    • This is one of the rare exceptions to the very high 1,4-regioselectivity usually obtained in the palladium-catalyzed oxidations of conjugated dienes; see refs 5b and 11a.
  • 44
    • 84985634168 scopus 로고
    • Control experiments showed that no allylic transposition in the products occurred under the reaction conditions; see: Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 579
    • Overman, L.E.1
  • 45
    • 2142788886 scopus 로고    scopus 로고
    • note
    • This corresponds to 7.5 equiv of HOAc to substrate.
  • 46
    • 2142795508 scopus 로고    scopus 로고
    • note
    • For a mechanistic discussion, and an explanation of the stereoselectivity, see refs 5b and 8a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.