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Volumn 10, Issue 18, 2008, Pages 3985-3988

Ring expansion of lactones and lactams via propiolate 1-carbon intercalation

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBON; INTERCALATING AGENT; LACTAM; LACTONE; PROPIOLIC ACID; PROPIONIC ACID DERIVATIVE;

EID: 55949129723     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8014682     Document Type: Article
Times cited : (12)

References (31)
  • 1
    • 42449130596 scopus 로고    scopus 로고
    • Recent reviews: a
    • Recent reviews: (a) Banwell, M. G. Pure Appl. Chem. 2008, 80, 669-679.
    • (2008) Pure Appl. Chem , vol.80 , pp. 669-679
    • Banwell, M.G.1
  • 4
    • 30744476469 scopus 로고    scopus 로고
    • (d) Inoue, M. Chem. Rev. 2005, 105, 4379-4405.
    • (2005) Chem. Rev , vol.105 , pp. 4379-4405
    • Inoue, M.1
  • 10
    • 0000517783 scopus 로고    scopus 로고
    • For an alternative two-carbon intercalation process involving the addition of simple acetylides to lactones or lactams followed by endocyclization, see: (a) Schreiber, S. L.; Kelly, S. E. Tetrahedron Lett. 1984, 25, 1757-1760.
    • For an alternative two-carbon intercalation process involving the addition of simple acetylides to lactones or lactams followed by endocyclization, see: (a) Schreiber, S. L.; Kelly, S. E. Tetrahedron Lett. 1984, 25, 1757-1760.
  • 22
    • 33845378280 scopus 로고    scopus 로고
    • A similar explanation was given for the superiority of the Keck lactonization conditions (DMAP/DMAP-HCl): (a) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
    • A similar explanation was given for the superiority of the Keck lactonization conditions (DMAP/DMAP-HCl): (a) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
  • 25
    • 61349156489 scopus 로고    scopus 로고
    • The seven-membered product 3b could not easily be distinguished from the alternative isomeric structure 8b by standard 1D NMR techniques. However, HMBC experiments clearly indicated a correlation between H-4 and C-2, which would not be observable in 8b (see Scheme 2).
    • The seven-membered product 3b could not easily be distinguished from the alternative isomeric structure 8b by standard 1D NMR techniques. However, HMBC experiments clearly indicated a correlation between H-4 and C-2, which would not be observable in 8b (see Scheme 2).
  • 26
    • 61349171014 scopus 로고    scopus 로고
    • 1H NMR chemical shifts of the alkene proton to those of 3fZ and 3fE as well as related literature compounds. See Supporting Information for a discussion of these assignments.
    • 1H NMR chemical shifts of the alkene proton to those of 3fZ and 3fE as well as related literature compounds. See Supporting Information for a discussion of these assignments.
  • 27
    • 61349132614 scopus 로고    scopus 로고
    • A vicinal coupling of 9.5 Hz between the adjacent ester-substituted methines was observed, consistent with a trans relationship. See Supporting Information for additional discussion of structural assignments.
    • A vicinal coupling of 9.5 Hz between the adjacent ester-substituted methines was observed, consistent with a trans relationship. See Supporting Information for additional discussion of structural assignments.
  • 28
    • 61349105077 scopus 로고    scopus 로고
    • The connectivity of endocyclization products 8g,h was established via HMBC correlations between the alkene proton (H-3) and C-5.
    • The connectivity of endocyclization products 8g,h was established via HMBC correlations between the alkene proton (H-3) and C-5.
  • 29
    • 37049046169 scopus 로고
    • For earlier examples of similar pyridine-ynone adducts, see: a
    • For earlier examples of similar pyridine-ynone adducts, see: (a) Crabtree, A.; Jackman, L. M.; Johnson, A. W. J. Chem. Soc. 1962, 4417-4420.
    • (1962) J. Chem. Soc , pp. 4417-4420
    • Crabtree, A.1    Jackman, L.M.2    Johnson, A.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.