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Volumn 2007, Issue 4, 2007, Pages 285-296

Organocatalyzed diastereoselective Henry reaction of enantiopure 4-oxoazetidine-2-carbaldehydes

Author keywords

Asymmetric induction; Henry reaction; Organocatalysis; lactams

Indexed keywords


EID: 33846114199     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.425     Document Type: Article
Times cited : (4)

References (54)
  • 2
    • 85069245061 scopus 로고    scopus 로고
    • The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
    • The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
  • 4
    • 85069251507 scopus 로고    scopus 로고
    • The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
    • The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
  • 5
    • 0042423395 scopus 로고    scopus 로고
    • Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus protease, thrombin, prostate specific antigen, and cell metastasis and as inhibitors of acyl-CoA cholesterol acyl transferase. For reviews, see: Veinberg, G, Vorona, M, Shestakova, I, Kanepe, I, Lukevics, E. Curr. Med. Chem. 2003, 10, 1741
    • Some of the more notable advances concern the development of mechanism-based serine protease inhibitors of elastase, cytomegalovirus protease, thrombin, prostate specific antigen, and cell metastasis and as inhibitors of acyl-CoA cholesterol acyl transferase. For reviews, see: Veinberg, G.; Vorona, M.; Shestakova, I.; Kanepe, I.; Lukevics, E. Curr. Med. Chem. 2003, 10, 1741.
  • 26
    • 11844259698 scopus 로고    scopus 로고
    • For selected reviews, see:, Mahrwald, R, Ed, Wiley-VCH: Weinheim
    • For selected reviews, see: Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004.
    • (2004) Modern Aldol Reactions
  • 43
    • 85069240939 scopus 로고    scopus 로고
    • For recents selected reviews, see: Tetrahedron 2006, 62, issues 2 and 3: Organocatalysis in organic synthesis, Kočovský, P.; Malkov, A. V. Guest Eds.
    • For recents selected reviews, see: Tetrahedron 2006, 62, issues 2 and 3: Organocatalysis in organic synthesis, Kočovský, P.; Malkov, A. V. Guest Eds.
  • 44
    • 47749122232 scopus 로고    scopus 로고
    • Berkessel, A, Gröger, H, Eds, Wiley-VCH: Weinheim
    • Asymmetric Organocatalysis; Berkessel, A., Gröger, H., Eds.; Wiley-VCH: Weinheim, 2005.
    • (2005) Asymmetric Organocatalysis
  • 49
    • 0034647707 scopus 로고    scopus 로고
    • The assignment of relative configuration based on the observed coupling constant for methine protons H3 and H4 is a very well established criterion in β-lactam chemistry. See, for example: Alcaide, B, Almendros, P, Salgado, N. R, Rodríguez-Vicente, A. J. Org. Chem, 2000, 65, 4453
    • The assignment of relative configuration based on the observed coupling constant for methine protons H3 and H4 is a very well established criterion in β-lactam chemistry. See, for example: Alcaide, B.; Almendros, P.; Salgado, N. R.; Rodríguez-Vicente, A. J. Org. Chem., 2000, 65, 4453.
  • 54
    • 85069244867 scopus 로고    scopus 로고
    • X-ray data of syn, )-4e: crystallized from ethyl acetate/n-hexane at 20°C; C20H20N2O8 (M r, 416.38, orthorhombic; space group, P2(1)2(1)2(1, a, 7.2996(15) Å, b, 14.392(3) Å; c, 19.190(4) Å; β, 90 deg, V, 2016.0(7) Å3; Z, 4; cd, 1.372 mg m-3; μ, 0.107 mm-1; F(000, 872. A transparent crystal of 0.45 x 0.09 x 0.04 mm3 was used. 3514 [R(int, 0.1395] independent reflections were collected on a Bruker Smart CCD difractomer using graphite-monochromated Mo-Kα radiation (λ, 0.71073 Å) operating at 50 Kv and 30 mA. Data were collected over a hemisphere of the reciprocal space by combination of three exposure sets. Each exposure of 20s and 30s covered 0.3 in ω. The structure was solved by direct methods and Fourier synthesis. It was refined by full-matrix least-squares procedures on F2 SHELXL-97, All
    • 2 (SHELXL-97). All non-hydrogen atoms were refined anisotropically and all hydrogen atoms were included in calculated positions and refined riding on the respective carbon or oxygen atoms. Final R(Rw) values were 0.0534 (0.1166) and 0.1973 (0.1596). CCDC-610275 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the http://www.ccdc.can.ac.uk/ conts/retrieving.html (or from the Cambridge Crystallographic Centre, 12 Union Road, Cambridge CB21EZ, UK; Fax (+44)1223-336033; or deposit@cccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.