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Volumn 69, Issue 6, 2004, Pages 1919-1939

A Three-Component, One-Pot Synthesis of Indolizidines and Related Heterocycles Via the [3+2] Cycloaddition of Nonstabilized Azomethine Ylides

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKYLATION; HYDROGEN; LITHIUM; SYNTHESIS (CHEMICAL);

EID: 1642403870     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030334h     Document Type: Article
Times cited : (56)

References (102)
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    • (b) Kanemasa, S.; Tsuge, O. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1993; Vol. 3, pp 99-159.
    • (1993) Advances in Cycloaddition , vol.3 , pp. 99-159
    • Kanemasa, S.1    Tsuge, O.2
  • 3
    • 0004136903 scopus 로고
    • Curran, D. P., Ed.; JAI Press: Greenwich CT
    • (c) Grigg, R.; Sridharan, V. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1993; Vol. 3, pp 161-204.
    • (1993) Advances in Cycloaddition , vol.3 , pp. 161-204
    • Grigg, R.1    Sridharan, V.2
  • 4
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK
    • (d) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, pp 1069-1109.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069-1109
    • Padwa, A.1
  • 5
    • 0000629986 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK
    • (e) Wade, P. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, pp 1111-1168.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1111-1168
    • Wade, P.A.1
  • 6
    • 0003525808 scopus 로고
    • Rahman, A., Ed.; Elsevier: Amsterdam, The Netherlands
    • (f) Pearson, W. H. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam, The Netherlands, 1988; Vol. 1, pp 323-358.
    • (1988) Studies in Natural Products Chemistry , vol.1 , pp. 323-358
    • Pearson, W.H.1
  • 7
    • 0002707988 scopus 로고
    • Curran, D. P., Ed.; JAI Press: Greenwich, CT
    • (g) Vedejs, E. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1988; Vol. 1, pp 33-51.
    • (1988) Advances in Cycloaddition , vol.1 , pp. 33-51
    • Vedejs, E.1
  • 8
    • 0004101860 scopus 로고
    • Padwa, A., Ed.; John Wiley & Sons: New York
    • (h) Lown, W. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp 653-733.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1 , pp. 653-733
    • Lown, W.J.1
  • 9
    • 1642271643 scopus 로고
    • Padwa, A., Ed.; John Wiley & Sons: New York
    • (i) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2, pp 227-387.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2 , pp. 227-387
    • Padwa, A.1
  • 23
    • 0035944163 scopus 로고    scopus 로고
    • For pyrrolizidines or indolizidines made from nonstabilized azomethine ylides (i.e. bearing only hydrogens or alkyl groups) see: (a) Castulik, J.; Marek, J.; Mazal, C. Tetrahedron 2001, 57, 8339-8347.
    • (2001) Tetrahedron , vol.57 , pp. 8339-8347
    • Castulik, J.1    Marek, J.2    Mazal, C.3
  • 61
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    • note
    • See the Supporting Information for an improved procedure for the preparation of 9.
  • 70
    • 85081427526 scopus 로고    scopus 로고
    • note
    • In the generation of nonstabilized azomethine ylides by fluoride-induced desilylation of N-(trimethylsilyl)methyl iminium salts, the added fluoride source typically must be anhydrous. See refs 1d and 2.
  • 81
    • 0001726634 scopus 로고
    • Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554-1555 and refs 29a, 29c, and 37c. Many other reports of water or halide as desilylating agents for N-(trimethylsilyl)methyl iminiums conspicuously lack enolizable hydrogens. For example see refs 4b, 4c, 20a, 20b, 29b, and 29d.
    • (1983) J. Org. Chem. , vol.48 , pp. 1554-1555
    • Smith, R.1    Livinghouse, T.2
  • 94
    • 85081429073 scopus 로고    scopus 로고
    • note
    • Interestingly, Torii (ref 30) reports a successful azomethine ylide cycloaddition involving the condensation of isobutyraldehyde with N-(trimethylsilylmethyl)benzylamine in THF, which presumably proceeds through iminium 51 in Scheme 12. In Torii's case, water or hydroxide are the likely desilylating agents, as opposed to chloride or bromide in our case.


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