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Volumn 68, Issue 16, 2003, Pages 6407-6410

Ring opening of nonactivated 2-(1-aminoalkyl) aziridines: Unusual regio- and stereoselective C-2 and C-3 cleavage

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVITY;

EID: 0043076447     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034440v     Document Type: Article
Times cited : (37)

References (30)
  • 14
    • 0026766134 scopus 로고
    • Only the ring opening of activated 2,3-aziridino alcohols by different hydride and methyl-transfer reagents led to regio- and stereoselective C-2 and C-3 cleavage, depending on the chelate effect of the reagent: (a) Tanner, D.; He, H. M.; Somfai, P. Tetrahedron 1992, 48, 6069.
    • (1992) Tetrahedron , vol.48 , pp. 6069
    • Tanner, D.1    He, H.M.2    Somfai, P.3
  • 19
    • 0034697199 scopus 로고    scopus 로고
    • The 1,2-amino alcohol moiety is a common structural component in naturally occurring and synthethic molecules, as well as being used as a chiral auxiliary: (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
    • (2000) Tetrahedron , vol.56 , pp. 2561
    • Bergmeier, S.C.1
  • 20
    • 0038468227 scopus 로고    scopus 로고
    • The 1,2-amino alcohol moiety is a common structural component in naturally occurring and synthethic molecules, as well as being used as a chiral auxiliary: (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
    • (1996) Chem. Rev. , vol.96 , pp. 835
    • Ager, D.J.1    Prakash, I.2    Schaad, D.R.3
  • 22
    • 0000911926 scopus 로고    scopus 로고
    • Concellón, J. M.; Bernad, P. L.; Riego, E.; Garcia-Granda, S.; Forcén-Acebal, A. J. Org. Chem. 2001, 66, 2764. A later alternative synthesis of N,N-dibenzylamino aziridines: Reetz, M. T.; Lee, W. K. Org. Lett. 2001, 3, 3119.
    • (2001) Org. Lett. , vol.3 , pp. 3119
    • Reetz, M.T.1    Lee, W.K.2
  • 26
    • 0042729057 scopus 로고    scopus 로고
    • note
    • 2 led to a 3/1 mixture of regioisomers.
  • 29
    • 33748664816 scopus 로고    scopus 로고
    • Previously, other N,N-dibenzylated aziridinium salts were proposed as intermediates in reactions of 2,3-epoxyamines: (a) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1997, 511. (b) Liu, Q.; Marchington, A. P.; Rayner, C. M. Tetrahedron 1997, 53, 15729.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 511
    • Liu, Q.1    Marchington, A.P.2    Boden, N.3    Rayner, C.M.4
  • 30
    • 0030734433 scopus 로고    scopus 로고
    • Previously, other N,N-dibenzylated aziridinium salts were proposed as intermediates in reactions of 2,3-epoxyamines: (a) Liu, Q.; Marchington, A. P.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1997, 511. (b) Liu, Q.; Marchington, A. P.; Rayner, C. M. Tetrahedron 1997, 53, 15729.
    • (1997) Tetrahedron , vol.53 , pp. 15729
    • Liu, Q.1    Marchington, A.P.2    Rayner, C.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.