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Volumn 7, Issue 3, 2001, Pages 611-621

Planar chirality: Cycloaddition and transannular reactions of optically active azoninones that contain (E)-olefins

Author keywords

Chirality; Cycloaddition; Hydroxylation; Lactams; Ring contraction

Indexed keywords

ALKALOID; ALKENE DERIVATIVE; AZONINONE DERIVATIVE; BICYCLO COMPOUND; CYCLOPROPANE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE; HYDROXYL GROUP; IMINE; INDOLIZIDINE DERIVATIVE; LACTAM; UNCLASSIFIED DRUG;

EID: 0035793247     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010202)7:3<611::AID-CHEM611>3.0.CO;2-9     Document Type: Article
Times cited : (43)

References (58)
  • 13
    • 0001080877 scopus 로고    scopus 로고
    • For further syntheses of unsaturated medium-sized ring lactams including some transannular reactions see: a) C. J. Deur , M. W. Miller, L. S. Hegedus, J. Org. Chem. 1996, 61, 2871;
    • (1996) J. Org. Chem. , vol.61 , pp. 2871
    • Deur, C.J.1    Miller, M.W.2    Hegedus, L.S.3
  • 21
    • 0006084872 scopus 로고    scopus 로고
    • note
    • Ratio of 3:4 after heating to 60°C: 3a:4a = 5:95 (4 h), 3b:4b = 1:13 (3 h), 3c:4c = 1:4.3 (3 h). Separation of 3 and 4 by column chromatography or HPLC, if necessary. In some experiments starting from pR-4, some pS-3 reamined as impurity. Usually, the reactant ratio (pS-3/pR-4) was completely transferred on generating the corresponding products (no epimerization).
  • 35
    • 33847583868 scopus 로고    scopus 로고
    • For spectral data of γ-butyrolactam 23, see the Supporting Information
    • For spectral data of γ-butyrolactam 23, see the Supporting Information.
  • 46
    • 33847592142 scopus 로고    scopus 로고
    • For detailed NOE data see the Supporting Information
    • For detailed NOE data see the Supporting Information.
  • 47
    • 0006084873 scopus 로고    scopus 로고
    • note
    • 1 (Figure 3).
  • 50
    • 33847594728 scopus 로고    scopus 로고
    • For spectral data of γ-butyrolactones 22 see the Supporting Information
    • For spectral data of γ-butyrolactones 22 see the Supporting Information.
  • 51
    • 0006073008 scopus 로고    scopus 로고
    • note
    • Generally, the lactones 22 can be used as intermediates to generate the desired indolizidinones 19; after hydrogenolytic removal of the benzylamine, a subsequent lactone-lactam conversion should lead to the desired bicyclic products.
  • 55
    • 0006119582 scopus 로고    scopus 로고
    • note
    • 1 (Figure 4).
  • 56
    • 0006114404 scopus 로고    scopus 로고
    • note
    • As a matter of principle, the lactam function can adopt four discrete arrangements: 2 x Z (pR and pS) and 2 x E (pR and pS) with respect to the oxygen and benzyl groups.
  • 58
    • 0001178865 scopus 로고    scopus 로고
    • and A. Deiters, C. Mück-Lichtenfeld, R. Fröhlich, D. Hoppe, Org. Lett. 2000, 2, 2415 (including kinetic measurements); force-field MM+ calculations had been carried out with Hyperchem by arranging C3 and C9 in a cis configuration with respect to the double-bond character of the lactam unit. Structures 11 and minor-11 as outlined in Scheme 5, data are given in Table 4. Potential trans-11 with C3 and C9 trans with respect to the double bond character of the lactam unit not shown.
    • (2000) Org. Lett. , vol.2 , pp. 2415
    • Deiters, A.1    Mück-Lichtenfeld, C.2    Fröhlich, R.3    Hoppe, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.