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Volumn 69, Issue 3, 2004, Pages 993-996

Synthesis of Optically Pure Highly Functionalized γ-Lactams via 2-Azetidinone-Tethered Iminophosphoranes

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; HYDROLYSIS; LITHIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 0842307395     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035623k     Document Type: Article
Times cited : (63)

References (51)
  • 7
    • 0002102562 scopus 로고
    • Georg, G. I., Ed.; VCH Publishers: New York
    • For reviews, see: (a) Ojima, I. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; p 197.
    • (1993) The Organic Chemistry of β-Lactams , pp. 197
    • Ojima, I.1
  • 14
    • 57249083927 scopus 로고    scopus 로고
    • For the applications of 4-oxoazetidine-2-carbaldehydes as efficient chiral synthons, see: (a) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. For a review on the chemistry of azetidine-2,3-diones, see:
    • (2001) Chem. Soc. Rev. , vol.30 , pp. 226
    • Alcaide, B.1    Almendros, P.2
  • 34
    • 0034595608 scopus 로고    scopus 로고
    • We have reported recently a base-promoted regiospecific C2-epimerization of cis-4-oxoazetidine-2-carbaldehydes to trans-4-oxoazetidine-2-carbaldehydes. See: Alcaide, B.; Aly, M. F.; Rodriguez, C.; Rodríguez-Vicente, A. J. Org. Chem. 2000, 65, 3453.
    • (2000) J. Org. Chem. , vol.65 , pp. 3453
    • Alcaide, B.1    Aly, M.F.2    Rodriguez, C.3    Rodríguez-Vicente, A.4
  • 38
    • 0034647707 scopus 로고    scopus 로고
    • 1H NMR spectra. The assignment of relative stereochemistry based on the observed coupling constant for methine protons H3 and H4 is a very well-established criterium in β-lactam chemistry. See, for example: Alcaide, B.; Almendros, P.; Salgado, N. R.; Rodriguez-Vincente, A. J. Org. Chem., 2000, 65, 4453.
    • (2000) J. Org. Chem. , vol.65 , pp. 4453
    • Alcaide, B.1    Almendros, P.2    Salgado, N.R.3    Rodriguez-Vincente, A.4
  • 41
    • 0346970848 scopus 로고    scopus 로고
    • For selected reviews on phosphazene chemistry, see: (a) Fresneda, P. M.; Molina, P. Synlett 2004, 1.
    • (2004) Synlett , pp. 1
    • Fresneda, P.M.1    Molina, P.2
  • 51
    • 0842319782 scopus 로고    scopus 로고
    • note
    • Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.


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