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Volumn 62, Issue 2-3, 2006, Pages 483-495

A [3,3]-sigmatropic process catalysed by acetate. The decarboxylative Claisen rearrangement

Author keywords

Acetate catalysed; Claisen rearrangement; Decarboxylation; Regiospecific allylation

Indexed keywords

ANION; SULFONE;

EID: 28944454547     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.073     Document Type: Article
Times cited : (20)

References (42)
  • 1
    • 4344610661 scopus 로고    scopus 로고
    • For a recent, comprehensive review of the Claisen rearrangement, see: A.M.M. Castro Chem. Rev. 104 2004 2939
    • (2004) Chem. Rev. , vol.104 , pp. 2939
    • Castro, A.M.M.1
  • 3
    • 13244259829 scopus 로고    scopus 로고
    • (b) For a recent review of the Ireland-Claisen rearrangement, and leading references, see: M.C. McIntosh Tetrahedron 58 2002 2905
    • (2002) Tetrahedron , vol.58 , pp. 2905
    • McIntosh, M.C.1
  • 5
    • 0034603016 scopus 로고    scopus 로고
    • (a) For Ireland-Claisen rearrangements of silyl ketene acetals derived from simple methyl allyl malonates involving desilylation and decarboxylation in a separate step, see: C. Fehr, and J. Galindo Angew. Chem., Int. Ed. 39 2000 569
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 569
    • Fehr, C.1    Galindo, J.2
  • 6
    • 4043177166 scopus 로고    scopus 로고
    • (b) For recent examples of regio- and enantioselective metal-catalysed decarboxylative allylation reactions, see: E.C. Burger, and J.A. Tunge Org. Lett. 6 2004 2603
    • (2004) Org. Lett. , vol.6 , pp. 2603
    • Burger, E.C.1    Tunge, J.A.2
  • 9
    • 18744415432 scopus 로고    scopus 로고
    • (e) For a review of transition metal-catalysed decarboxylative additions of enolates, see: J.A. Tunge, and E.C. Burger Eur. J. Org. Chem. 2005 1715
    • (2005) Eur. J. Org. Chem. , pp. 1715
    • Tunge, J.A.1    Burger, E.C.2
  • 13
    • 28944451141 scopus 로고    scopus 로고
    • Purchased from Aldrich Chemical Co.
    • Purchased from Aldrich Chemical Co.
  • 30
    • 28944445637 scopus 로고    scopus 로고
    • unpublished results.
    • We have found subsequently that two equivalents of the mixed malonate conjugate base are generally sufficient for efficient tosylation with TsF: Paina, F., unpublished results.
    • Paina, F.1
  • 31
    • 28944453859 scopus 로고    scopus 로고
    • note
    • Compounds 12d and 12h were formed as 70:30 mixtures of diastereoisomers; compound 12i was formed as a 61:39 mixture of diastereoisomers. Major isomers have not been assigned in these cases.
  • 32
    • 28944441622 scopus 로고    scopus 로고
    • note
    • Yields cited for 11 are based on tosyl fluoride; yields in parentheses are for recovered 10 and are calculated from the total recoverable amount based on the yield of 11 and the amount of 10 used (4.5 equiv with respect to TsF). For example, a 70% yield of 11 means the total recoverable amount of 10 is (4.5-0.7)=3.8 equiv; 74% recovery means that (0.74×3.8=2.81 equiv) of 10 was recovered.
  • 37
    • 0038020764 scopus 로고
    • For metal-catalysed allylation reactions of methyl tosylacetate, see: (a) S.A. Godleski, and E.B. Villhauer J. Org. Chem. 49 1984 2246
    • (1984) J. Org. Chem. , vol.49 , pp. 2246
    • Godleski, S.A.1    Villhauer, E.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.