메뉴 건너뛰기




Volumn 8, Issue 5, 2006, Pages 995-998

Intramolecular cyclopropanation of unsaturated terminal aziridines

Author keywords

[No Author keywords available]

Indexed keywords


EID: 33644950248     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060101n     Document Type: Article
Times cited : (32)

References (48)
  • 6
    • 0000673216 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin
    • Also, for reviews on enantioselective aziridination, see: (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 607-618
    • Jacobsen, E.N.1
  • 13
    • 0242475011 scopus 로고    scopus 로고
    • Florio, S., Ed.
    • For recent reviews on aziridinyl and oxiranyl anions, see: (a) Oxiranyl and aziridinyl anions as reactive intermediates in synthetic organic chemistry. Florio, S., Ed.; Tetrahedron 2003, 59, 9683-9864.
    • (2003) Tetrahedron , vol.59 , pp. 9683-9864
  • 19
    • 1342345086 scopus 로고    scopus 로고
    • Carbene reactivity has been observed for ring-fused aziridines, where 2H-azirine formation is less likely; see: Müller, P.; Riegert, D.; Bernardinelli, G. Helv. Chim. Acta 2004, 87, 227-239.
    • (2004) Helv. Chim. Acta , vol.87 , pp. 227-239
    • Müller, P.1    Riegert, D.2    Bernardinelli, G.3
  • 21
  • 32
    • 33644934175 scopus 로고    scopus 로고
    • note
    • Determined by NOE analysis and by comparison with the analogous epoxide cyclopropanation product; see ref 13a.
  • 33
    • 33644962473 scopus 로고    scopus 로고
    • note
    • Use of LDA under these conditions gave 30% yield of amine 8.
  • 39
    • 33644949695 scopus 로고    scopus 로고
    • Isolated as a single diastereomer. Structure supported by X-ray crystallographic analysis: CCDC 292434 available at http://www.ccdc. cam.ac.uk.
  • 40
    • 33644951023 scopus 로고    scopus 로고
    • note
    • 2, quenching directly after addition of the aziridine 9 (1 h) indicated incomplete reaction; 9 (52%), amine 10 (10%), and dimer 11 (22%) were obtained.
  • 41
    • 33644951694 scopus 로고    scopus 로고
    • note
    • Use of N-Ts aziridine 6 under these conditions gave a 47% yield of amine 8.
  • 44
    • 33644937861 scopus 로고    scopus 로고
    • note
    • 2O) gave the bicyclic amine. (29) Determined by chiral GC analysis.
  • 46
    • 0001373505 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • (b) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1992; Vol. 5, pp 899-970.
    • (1992) Comprehensive Organic Synthesis , vol.5 , pp. 899-970
    • Hudlicky, T.1    Reed, J.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.