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Volumn 6, Issue 11, 2008, Pages 1981-1993

A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; ANTIBIOTICS; EPOXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 43749091301     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b802310g     Document Type: Article
Times cited : (19)

References (102)
  • 50
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    • A. K. Yudin, Wiley-VCH, Weinheim, pp. 315; see also ref. 16 for further discussions For recent reviews on sulfonium ylide epoxidation, see:
    • For a review on vinyl epoxides, see: B. Olofsson and P. Somfai, in Aziridines and Epoxides in Organic Synthesis, ed., A. K. Yudin, Wiley-VCH, Weinheim, 2006, pp. 315
    • (2006) Aziridines and Epoxides in Organic Synthesis, Ed.
    • Olofsson, B.1    Somfai In, P.2
  • 59
    • 4644231912 scopus 로고    scopus 로고
    • For the use and comments in ylide-promoted epoxidation by a pre-formed sulfonium salt in water, see:
    • C. Faltin E. M. Fleming S. J. Connon J. Org. Chem. 2004 69 6496
    • (2004) J. Org. Chem. , vol.69 , pp. 6496
    • Faltin, C.1    Fleming, E.M.2    Connon, S.J.3
  • 65
    • 43749094859 scopus 로고    scopus 로고
    • N2′ addition of water to the epoxide 3g to give 5 after cyclisation For selected references concerning the intermolecular ring-opening reaction of vinyl epoxides by alcohol or water, see:
    • J. B. Sweeney A. E. Nadany N. B. Carter J. Chem. Soc., Perkin Trans. 1 2002 2324
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 2324
    • Sweeney, J.B.1    Nadany, A.E.2    Carter, N.B.3
  • 75
    • 0344813188 scopus 로고
    • Alternatively, the direct intramolecular addition of the amide moiety onto the carbocation intermediate in Scheme 5 could be envisaged When slow epoxidation occurred in the presence of NaOH as a base, the formation of a Cannizzaro-type product (benzoic acid) and a Willamson-type product from allylic bromide 2a was observed (see ESI for details)
    • C. R. Hauser T. C. Adams J. Org. Chem. 1977 42 3029
    • (1977) J. Org. Chem. , vol.42 , pp. 3029
    • Hauser, C.R.1    Adams, T.C.2
  • 89
    • 0043287923 scopus 로고    scopus 로고
    • 2 and a nucleophilic phosphine ligand was also proposed as an inhibitation process: see ref. 38a
    • Z.-X. Jiang F.-L. Quing J. Fluorine Chem. 2003 123 57
    • (2003) J. Fluorine Chem. , vol.123 , pp. 57
    • Jiang, Z.-X.1    Quing, F.-L.2
  • 92
    • 0037195680 scopus 로고    scopus 로고
    • For a review on the formation of polysubsituted alkenes, see:
    • B. Olofsson P. Somfai J. Org. Chem. 2002 67 8574
    • (2002) J. Org. Chem. , vol.67 , pp. 8574
    • Olofsson, B.1    Somfai, P.2
  • 94
    • 15244341482 scopus 로고    scopus 로고
    • for cross-coupling reaction of zinc species, see:
    • E.-I. Negishi Dalton Trans. 2005 827
    • (2005) Dalton Trans. , pp. 827
    • Negishi, E.-I.1
  • 102
    • 0027997412 scopus 로고
    • The synthesis of the aldehyde derivative 17 (via 15 and 16) was previously described by Scolastico and co-workers in 7 linear steps: see ref. 17c
    • S. V. Ley J. Norman W. P. Griffith S. P. Marsden Synthesis 1994 639
    • (1994) Synthesis , pp. 639
    • Ley, S.V.1    Norman, J.2    Griffith, W.P.3    Marsden, S.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.