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Volumn 8, Issue 22, 2006, Pages 5145-5148

New route to azaspirocycles via the organolithium-mediated conversion of β-alkoxy aziridines into cyclopentenyl amines

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EID: 33750908043     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062073e     Document Type: Article
Times cited : (17)

References (34)
  • 8
    • 0001318042 scopus 로고    scopus 로고
    • For reviews containing information on the chemistry of lithiated aziridines, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303.
    • (1996) Chem. Rev. , vol.96 , pp. 3303
    • Satoh, T.1
  • 10
    • 33750903570 scopus 로고    scopus 로고
    • (c) For a special issue on oxiranyl and aziridinyl anions, see: Tetrahedron 2003, 9693-9847.
    • (2003) Tetrahedron , pp. 9693-9847
  • 17
    • 33750926332 scopus 로고    scopus 로고
    • note
    • H 3.31 (s) for trans-12. Thus, for the cis aziridines, the CHN proton appears more downfield and is a doublet (J = 2.5 Hz) compared to the trans aziridines.
  • 28
    • 0033927135 scopus 로고    scopus 로고
    • Bromides 25 and 26 are commercially available. Bromide 27 was prepared by silylation of the alcohol (see Supporting Information). For synthesis of the alcohol, see: Tietze, L. F.; Schirok, H.; Wöhrmann, M.; Schrader, K. Eur. J. Org. Chem. 2000, 2433.
    • (2000) Eur. J. Org. Chem. , pp. 2433
    • Tietze, L.F.1    Schirok, H.2    Wöhrmann, M.3    Schrader, K.4
  • 31
    • 2542478224 scopus 로고    scopus 로고
    • For an example of the use of mixtures of two organolithium reagents in a related reaction of an epoxide, see: Hodgson, D. M.; Paruch, E. Tetrahedron 2004, 60, 5185.
    • (2004) Tetrahedron , vol.60 , pp. 5185
    • Hodgson, D.M.1    Paruch, E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.