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Volumn 64, Issue 6, 1999, Pages 1831-1842

Competitive mechanisms and origins of stereocontrol in the [2 + 2] thermal cycloaddition between imines and keteniminium cations. A complementary entry to 2-azetidinones (β-lactams) and related compounds

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL BOND; CYCLIZATION; MATHEMATICAL COMPUTING; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033583273     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9815002     Document Type: Article
Times cited : (35)

References (99)
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    • (a) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 85-122.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 85-122
    • Ghosez, L.1    Marchand-Brynaert, J.2
  • 46
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    • Trost, B., Hutchinson, C. R., Eds.; Pergamon Press: New York
    • (c) Ghosez, L. In Organic Synthesis: Today and Tomorrow; Trost, B., Hutchinson, C. R., Eds.; Pergamon Press: New York, 1981.
    • (1981) Organic Synthesis: Today and Tomorrow
    • Ghosez, L.1
  • 47
    • 0344922120 scopus 로고    scopus 로고
    • note
    • These very promising results are based on iminium salts derived from (2S)-(methoxymethyl)pyrrolidine, and have been reported by the Ghosez's group. See ref 14a and footnote 222 therein.
  • 59
    • 0001192473 scopus 로고    scopus 로고
    • Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York
    • (b) Bartolotti, L. J.; Fluchick, K. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1996; Vol. 7, pp 187-216.
    • (1996) Reviews in Computational Chemistry , vol.7 , pp. 187-216
    • Bartolotti, L.J.1    Fluchick, K.2
  • 71
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    • Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York
    • (c) Cramer, C. J.; Truhlar, D. G. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1995; Vol. VI, pp 1-72.
    • (1995) Reviews in Computational Chemistry , vol.6 , pp. 1-72
    • Cramer, C.J.1    Truhlar, D.G.2
  • 86
    • 0345722032 scopus 로고    scopus 로고
    • Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, UK
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    • CSD User Manuals
  • 90
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    • de Mejijere, A., Blechert, S., Eds.; Kluwer Academic Publishers: Dordrecht
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  • 93
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    • note
    • We are grateful to one reviewer for suggesting the possible effect of this equilibration between both intermediates on the stereochemical outcome.
  • 94
    • 0031593029 scopus 로고    scopus 로고
    • Mayr, Würthwein, et al. have recently reported a combined NMR and computational study that supports this structure for iminium ion pairs. See: Mayr, H.; Ofial, A. R.; Würthwein, E.-U.; Aust, N. C. J. Am. Chem. Soc. 1997, 119, 12727.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12727
    • Mayr, H.1    Ofial, A.R.2    Würthwein, E.-U.3    Aust, N.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.