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Volumn , Issue 14 SPEC. ISS., 2008, Pages 2264-2270

Asymmetric synthesis of 3,4-annulated cyclopentenones from cycloalkenyl ketones and vinyl carbamates by diastereoselective carbonyl addition/conrotatory 4π ring closure

Author keywords

Asymmetric synthesis; Carbanion; Cyclopentenones; Electrocyclic reaction; Torquoselectivity

Indexed keywords

KETONES;

EID: 48549100206     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067150     Document Type: Article
Times cited : (3)

References (57)
  • 1
    • 0034610759 scopus 로고    scopus 로고
    • Cyclopentenone-derived prostaglandins: (a) Rossi, A.; Kapahi, P.; Natoli, G.; Takahashi, T.; Chen, Y.; Karin, M.; Santoro, M. G. Nature 2000, 403, 103.
    • Cyclopentenone-derived prostaglandins: (a) Rossi, A.; Kapahi, P.; Natoli, G.; Takahashi, T.; Chen, Y.; Karin, M.; Santoro, M. G. Nature 2000, 403, 103.
  • 7
    • 0037395377 scopus 로고    scopus 로고
    • Review: a
    • Review: (a) Tius, M. A. Acc. Chem. Res. 2003, 36, 284.
    • (2003) Acc. Chem. Res , vol.36 , pp. 284
    • Tius, M.A.1
  • 9
    • 21844434234 scopus 로고    scopus 로고
    • For further reading on the Nazarov cyclization, see also: (c) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577.
    • For further reading on the Nazarov cyclization, see also: (c) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577.
  • 12
    • 0028132989 scopus 로고    scopus 로고
    • In a more general way the Piancatelli reaction can be considered as a Nazarov reaction (transformation of furfuryl alcohols to cyclopentenones, review: (f) Piancatelli, G, D'Auria, M, D'Onofrio, F. Synthesis 1994, 867
    • In a more general way the Piancatelli reaction can be considered as a Nazarov reaction (transformation of furfuryl alcohols to cyclopentenones); review: (f) Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867.
  • 16
    • 33746279278 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 6017.
    • (2005) Angew. Chem , vol.117 , pp. 6017
  • 17
    • 48549083662 scopus 로고    scopus 로고
    • Another example for the addition of a nucleophilic carbene to a vinyl ketene: (d) Rigby, J. H.; Wang, Z. Org. Lett. 2003, 3, 263.
    • Another example for the addition of a nucleophilic carbene to a vinyl ketene: (d) Rigby, J. H.; Wang, Z. Org. Lett. 2003, 3, 263.
  • 19
    • 8744302169 scopus 로고    scopus 로고
    • Angew. Chem. 2002, 114, 1610.
    • (2002) Angew. Chem , vol.114 , pp. 1610
  • 21
    • 2442644023 scopus 로고    scopus 로고
    • Further articles about torquoselectivity in the synthesis of cyclopentenones: (b) López, C. S.; Faza, O. N.; York, D. M.; de Lera, A. R. J. Org. Chem. 2004, 69, 3635.
    • Further articles about torquoselectivity in the synthesis of cyclopentenones: (b) López, C. S.; Faza, O. N.; York, D. M.; de Lera, A. R. J. Org. Chem. 2004, 69, 3635.
  • 29
  • 30
    • 0000983397 scopus 로고    scopus 로고
    • 4 is described: (b) Hart, S. A.; Sabat, M.; Etzkorn, F. A. J. Org. Chem. 1998, 63, 7580.
    • 4 is described: (b) Hart, S. A.; Sabat, M.; Etzkorn, F. A. J. Org. Chem. 1998, 63, 7580.
  • 31
    • 48549083931 scopus 로고    scopus 로고
    • A partial base-induced epimerization of 6ca may be the origin.
    • A partial base-induced epimerization of 6ca may be the origin.
  • 32
    • 48549102151 scopus 로고    scopus 로고
    • X-ray crystal structure analysis for 6af: formula C 29H38O2Si, M, 446.68, colorless crystal 0.30 x 0.25 x 0.10 mm, a, 10.154(1, b, 16.328 (1, c, 15.949 (1) Å, β, 94.90 (1)°, V, 2634.6 (3) Å3, ρcalc, 1.126 g cm3, μ, 0.943 mm-1, empirical absorption correction (0.765 ≤ T ≤ 0.912, Z, 4, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K ω and φ scans, 21759 reflections collected (±h, ±k, ±l, sin θ)/λ, 0.60 Å-1, 7576 independent (Rint, 0.034) and 7417 observed reflections [I 2 σ(I, 587 refined parameters, R, 0.035, wR 2, 0.094, Flack parameter 0.04 (2, max. residual electron density 0.16, 0.13) eÅ-3
    • -3, two almost identical molecules in the asymmetric unit, hydrogen atoms calculated and refined as riding atoms. CCDC 670192 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk.
  • 41
    • 0004150157 scopus 로고    scopus 로고
    • University of Göttingen: Göttingen
    • Sheldrick, G. M. SHELXL-97; University of Göttingen: Göttingen, 1997.
    • (1997) SHELXL-97
    • Sheldrick, G.M.1
  • 42
    • 48549088746 scopus 로고    scopus 로고
    • Brüggemann, M. Ph.D. Thesis; University of Münster: Münster, 2000; graphic programme Mopict.
    • Brüggemann, M. Ph.D. Thesis; University of Münster: Münster, 2000; graphic programme Mopict.
  • 44
    • 0039169615 scopus 로고
    • Angew. Chem. 1994, 106, 1815.
    • (1994) Angew. Chem , vol.106 , pp. 1815
  • 46
    • 48549088028 scopus 로고    scopus 로고
    • Ph.D. Thesis; University of Münster: Münster
    • Reuber, J. Ph.D. Thesis; University of Münster: Münster, 2004.
    • (2004)
    • Reuber, J.1
  • 47
    • 48549095237 scopus 로고    scopus 로고
    • Siemer, M. Diploma Thesis; University of Munster: Münster, 2001.
    • (a) Siemer, M. Diploma Thesis; University of Munster: Münster, 2001.
  • 48
    • 48549099946 scopus 로고    scopus 로고
    • See also ref. 8b for comparison
    • (b) See also ref. 8b for comparison.
  • 52
    • 0001507942 scopus 로고
    • Angew. Chem. 1987, 99, 1186.
    • (1987) Angew. Chem , vol.99 , pp. 1186
  • 53
    • 48549090213 scopus 로고
    • Ph.D. Thesis; University of Marburg: Marburg
    • Schmitz, A. Ph.D. Thesis; University of Marburg: Marburg, 1991.
    • (1991)
    • Schmitz, A.1
  • 57
    • 0001947119 scopus 로고    scopus 로고
    • and references cited therein
    • Paquette, L. A. Eur. J. Org. Chem. 1998, 1709; and references cited therein.
    • (1998) Eur. J. Org. Chem , pp. 1709
    • Paquette, L.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.