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Volumn 64, Issue 9, 1999, Pages 3181-3189

Aziridination of activated imines with monocarbonyl iodonium ylides generated from (Z)-(2-acetoxyvinyl)iodonium salts via ester exchange: Stereoselective synthesis of 2-acylaziridines

Author keywords

[No Author keywords available]

Indexed keywords

2 ACYLAZIRIDINE DERIVATIVE; AZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033617424     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982346m     Document Type: Article
Times cited : (42)

References (78)
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    • For reaction of stable iodonium ylides, see: (a) Koser, G. F.; Yu, S.-M. J. Org. Chem. 1975, 40, 1166.
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  • 27
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    • a value of phenyliodonium 4,4-dimethyl-2,6-dioxocyclohexanide is 0.72. See: Kalnin, S. V.; Neilands, O. J. Org. Chem. USSR 1971, 7, 1668.
    • (1971) J. Org. Chem. USSR , vol.7 , pp. 1668
    • Kalnin, S.V.1    Neilands, O.2
  • 29
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    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford
    • (b) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 7, pp 47-93.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.7 , pp. 47-93
    • Padwa, A.1    Woolhouse, A.D.2
  • 30
  • 31
    • 0001346991 scopus 로고
    • For synthesis of aziridines via the reaction of an imine with an ylide, see: (a) Franzen, V.; Driesen, H.-E. Chem. Ber. 1963, 96, 1881.
    • (1963) Chem. Ber. , vol.96 , pp. 1881
    • Franzen, V.1    Driesen, H.-E.2
  • 45
    • 0345428761 scopus 로고    scopus 로고
    • note
    • The reported semiempirical AM1 calculations of the atomic net charges of benzaldehyde, N-benzylideneaniline 3a, and N-tosylimine 3j predict the following order of reactivity toward nucleophiles, PhCH= NTs 3j > PhCHO > PhCH=NPh 3a. See ref 8h.
  • 46
    • 0344135124 scopus 로고    scopus 로고
    • note
    • Reaction of 1b with EtOLi in THF-DMSO at -30 °C in the presence of styrene (10 equiv) yielded no the addition products, i.e., cyclopropanes, and gave 7 (55%, E:Z = 43:57).
  • 49
    • 0001697362 scopus 로고
    • The reasons for the influence of the counterion of the iodonium salt on the stereochemistry of the reaction is not clear. For similar effects of counteranion, see: (a) Bergelson, L. D.; Barsukov, L. I.; Shemayakin, M. M. Tetrahedron Lett. 1967, 23, 2709. (b) Still, W. C.; Novack, V. J. J. Am. Chem. Soc. 1981, 103, 1283. Ward, W. J.; McEwen, W. E. J. Org. Chem. 1990, 55, 493. Bellucci, G.; Chiappe, C.; Moro, G. L. Tetrahedron Lett. 1996, 37, 4225.
    • (1967) Tetrahedron Lett. , vol.23 , pp. 2709
    • Bergelson, L.D.1    Barsukov, L.I.2    Shemayakin, M.M.3
  • 50
    • 0009717830 scopus 로고
    • The reasons for the influence of the counterion of the iodonium salt on the stereochemistry of the reaction is not clear. For similar effects of counteranion, see: (a) Bergelson, L. D.; Barsukov, L. I.; Shemayakin, M. M. Tetrahedron Lett. 1967, 23, 2709. (b) Still, W. C.; Novack, V. J. J. Am. Chem. Soc. 1981, 103, 1283. Ward, W. J.; McEwen, W. E. J. Org. Chem. 1990, 55, 493. Bellucci, G.; Chiappe, C.; Moro, G. L. Tetrahedron Lett. 1996, 37, 4225.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1283
    • Still, W.C.1    Novack, V.J.2
  • 51
    • 0001388593 scopus 로고
    • The reasons for the influence of the counterion of the iodonium salt on the stereochemistry of the reaction is not clear. For similar effects of counteranion, see: (a) Bergelson, L. D.; Barsukov, L. I.; Shemayakin, M. M. Tetrahedron Lett. 1967, 23, 2709. (b) Still, W. C.; Novack, V. J. J. Am. Chem. Soc. 1981, 103, 1283. Ward, W. J.; McEwen, W. E. J. Org. Chem. 1990, 55, 493. Bellucci, G.; Chiappe, C.; Moro, G. L. Tetrahedron Lett. 1996, 37, 4225.
    • (1990) J. Org. Chem. , vol.55 , pp. 493
    • Ward, W.J.1    McEwen, W.E.2
  • 52
    • 0029950745 scopus 로고    scopus 로고
    • The reasons for the influence of the counterion of the iodonium salt on the stereochemistry of the reaction is not clear. For similar effects of counteranion, see: (a) Bergelson, L. D.; Barsukov, L. I.; Shemayakin, M. M. Tetrahedron Lett. 1967, 23, 2709. (b) Still, W. C.; Novack, V. J. J. Am. Chem. Soc. 1981, 103, 1283. Ward, W. J.; McEwen, W. E. J. Org. Chem. 1990, 55, 493. Bellucci, G.; Chiappe, C.; Moro, G. L. Tetrahedron Lett. 1996, 37, 4225.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4225
    • Bellucci, G.1    Chiappe, C.2    Moro, G.L.3
  • 67
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    • Bond length of I-O of the adduct 12 is 2.59(2) Å. See: Zhu, S.-Z. Heteroatom Chem. 1994, 5, 9.
    • (1994) Heteroatom Chem. , vol.5 , pp. 9
    • Zhu, S.-Z.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.