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Volumn 9, Issue 11, 2007, Pages 2111-2114

Alkyl C-O ring cleavage of bicyclic β-lactones with normant reagents: Synthesis of a merck IND intermediate

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EID: 34250673592     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070572p     Document Type: Article
Times cited : (15)

References (52)
  • 3
    • 2342504471 scopus 로고    scopus 로고
    • For more recent advances, see: c
    • For more recent advances, see: (c) Zhu, C.; Shen, X.; Nelson, S. G. J. Am. Chem. Soc. 2004, 126, 5352.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5352
    • Zhu, C.1    Shen, X.2    Nelson, S.G.3
  • 4
    • 11144311055 scopus 로고    scopus 로고
    • Wilson, J. E.; Fu, G. Agnew. Chem., Int. Ed. 2004, 43, 6358.
    • (d) Wilson, J. E.; Fu, G. Agnew. Chem., Int. Ed. 2004, 43, 6358.
  • 20
    • 34250685564 scopus 로고    scopus 로고
    • See also ref 1f
    • (c) See also ref 1f.
  • 22
    • 0037178969 scopus 로고    scopus 로고
    • For additions of heteroatom nucleophiles to bicyclic β-lactones, see: a, 7075. For other examples of additions to monocyclic-β-lactones, see
    • For additions of heteroatom nucleophiles to bicyclic β-lactones, see: (a) Yokota, Y.; Cortez, G. S.; Romo, D. Tetrahedron 2002, 58, 7075. For other examples of additions to monocyclic-β-lactones, see:
    • (2002) Tetrahedron , vol.58
    • Yokota, Y.1    Cortez, G.S.2    Romo, D.3
  • 23
    • 34250677885 scopus 로고    scopus 로고
    • ref 2
    • (b) ref 2.
  • 36
    • 34250684378 scopus 로고    scopus 로고
    • The report from the Goodman group (ref 7b) made extensive use of chloro Grignard-derived cuprates but no rationalization was provided.
    • The report from the Goodman group (ref 7b) made extensive use of chloro Grignard-derived cuprates but no rationalization was provided.
  • 40
    • 34250672197 scopus 로고    scopus 로고
    • Reference 5
    • (d) Reference 5.
  • 41
    • 34250671345 scopus 로고    scopus 로고
    • Nelson previously employed similar conditions for additions to monocyclic-β-lactones, see ref 7a
    • Nelson previously employed similar conditions for additions to monocyclic-β-lactones, see ref 7a.
  • 42
    • 34250641711 scopus 로고    scopus 로고
    • In this instance, the dioxolane was prone to hydrolysis during reaction workup
    • In this instance, the dioxolane was prone to hydrolysis during reaction workup.
  • 43
    • 33947434903 scopus 로고
    • For the earliest report of magnesium halide opening of β-lactones, see
    • For the earliest report of magnesium halide opening of β-lactones, see: Gresham, T. L.; Jansen, J. E.; Shaver, F. W.; Bankert, R. A. J. Am. Chem. Soc. 1949, 71, 2807.
    • (1949) J. Am. Chem. Soc , vol.71 , pp. 2807
    • Gresham, T.L.1    Jansen, J.E.2    Shaver, F.W.3    Bankert, R.A.4
  • 48
    • 85077990318 scopus 로고    scopus 로고
    • For a review describing Grignard reagents that are difficult to generate with chemically activated magnesium, see: Lai, Y. Synthesis 1981, 585
    • For a review describing Grignard reagents that are difficult to generate with chemically activated magnesium, see: Lai, Y. Synthesis 1981, 585.
  • 49
    • 34250690640 scopus 로고    scopus 로고
    • Employing <0.1 equiv of 1,2-dibromoethane to further minimize MgXBr concentration led to lower conversion to the Grignard reagent.
    • Employing <0.1 equiv of 1,2-dibromoethane to further minimize MgXBr concentration led to lower conversion to the Grignard reagent.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.