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Volumn 3, Issue 21, 2005, Pages 3937-3947

Acid-catalysed formation of tricyclic N,S-acetals in imidazolinone series based on the use of the unprecedented N-acyliminium ion cascade reaction involving transposition, heterocyclisation and π-cyclisation

Author keywords

[No Author keywords available]

Indexed keywords

ACID-CATALYSED DOMINO REACTION; HETEROCYCLISATION; METHYL TRANSPOSITION; TRICYCLIC N,S-ACETALS;

EID: 27844550718     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508214e     Document Type: Article
Times cited : (21)

References (53)
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    • ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, ch. 4.2
    • (b) D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 4, ch. 4.2;
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Curran, D.P.1
  • 7
    • 77957077000 scopus 로고
    • ed. A. Brossi, Academic Press, New York, ch. 4
    • (a) For representatives reviews in this area, see: H. Hiemstra and W. N. Speckamp, in The Alkaloids, ed. A. Brossi, Academic Press, New York, 1988, vol. 32, ch. 4, pp. 271-339;
    • (1988) The Alkaloids , vol.32 , pp. 271-339
    • Hiemstra, H.1    Speckamp, W.N.2
  • 9
    • 0001673091 scopus 로고
    • ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford
    • (c) H. Hiemstra and W. N. Speckamp, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 2, pp. 1047-1082;
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 10
    • 0001513757 scopus 로고    scopus 로고
    • ed. G. Helmchen, R. W. Hoffmann, J. Muzler and E. Schaumann, Thieme, Stuttgart
    • (d) H. Koning and W. N. Speckamp, in Stereoselective Synthesis [Houben-Weyl], ed. G. Helmchen, R. W. Hoffmann, J. Muzler and E. Schaumann, Thieme, Stuttgart, 1996, vol. 3, pp. 1952-2010;
    • (1996) Stereoselective Synthesis [Houben-Weyl] , vol.3 , pp. 1952-2010
    • Koning, H.1    Speckamp, W.N.2
  • 12
    • 0008001042 scopus 로고
    • (a) For C-N bonds forming via the N-acyliminium chemistry, see: P. Aeberli and W. J. Houlihan, J. Org. Chem., 1968, 33, 2402;
    • (1968) J. Org. Chem. , vol.33 , pp. 2402
    • Aeberli, P.1    Houlihan, W.J.2
  • 30
    • 0141826237 scopus 로고    scopus 로고
    • For C-O/C-N and/or C-S linkages forming, via the N-acyliminium species see: (s) N. Mizutani, W.-H. Chiou and I. Ojima, Org. Lett., 2002, 4, 4575;
    • (2002) Org. Lett. , vol.4 , pp. 4575
    • Mizutani, N.1    Chiou, W.-H.2    Ojima, I.3
  • 33
    • 27844449193 scopus 로고    scopus 로고
    • note
    • (b) Another example of this process was reported recently during their synthesis of azabicyclo[4.4.0]alkane amino acids by Rh-catalyzed cyclocarbonylation of amide-olefins. For this end, see ref. 4s, above.
  • 36
    • 0037930947 scopus 로고
    • Only one report concerning similar phenomenon using a tandem aza-Cope isomerisation/O-cyclisation was pointed in the literature. See H. Ent, H. De Koning and W. N. Speckamp, Heterocycles, 1990, 30, 501.
    • (1990) Heterocycles , vol.30 , pp. 501
    • Ent, H.1    De Koning, H.2    Speckamp, W.N.3
  • 41
    • 27844442338 scopus 로고    scopus 로고
    • note
    • 2-S functionality cleavage, was recovered in appreciable quantity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.