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Volumn 7, Issue 6, 2005, Pages 1153-1156

Substituted aziridines by lithiation-electrophile trapping of terminal aziridines

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; AZIRIDINE DERIVATIVE; HYDROGEN; LITHIUM; LITHIUM 2,2,6,6 TETRAMETHYLPIPERIDIDE; UNCLASSIFIED DRUG;

EID: 18244376859     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050060f     Document Type: Article
Times cited : (56)

References (48)
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    • 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. (d) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 607-618
    • Jacobsen, E.N.1
  • 7
    • 0042881024 scopus 로고    scopus 로고
    • 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. (d) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
    • (2003) Chem. Rev. , vol.103 , pp. 2905-2919
    • Müller, P.1    Fruit, C.2
  • 17
    • 18244376456 scopus 로고    scopus 로고
    • note
    • 10 80%) of a 1.7:1 trans/cis mixture of α,β-aziridinylsilanes.
  • 18
    • 18244369598 scopus 로고    scopus 로고
    • note
    • 3SiCl (3 equiv) in THF, the N-Boc aziridine of 1-hexene could be successfully silylated at -78°C (silylation was unsuccessful at 0°C) in 1 h (69%, >99% trans:cis), but this could not be usefully extended to other electrophiles.
  • 22
    • 18244370370 scopus 로고    scopus 로고
    • note
    • HH = 8 Hz for related N-Ts α,β-aziridinylsilanes.
  • 26
    • 18244399964 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude reaction mixtures showed substantial byproduct formation.
  • 27
    • 18244375981 scopus 로고    scopus 로고
    • note
    • 2O or EtOAc) gave the α,β-aziridinylsilane.
  • 28
    • 18244402034 scopus 로고    scopus 로고
    • note
    • Determined by specific rotation comparison of the starting enantioenriched (S)-1-(tert-butylsulfonyl)-2-decylaziridine and a sample prepared by TBAF-mediated desilylation of the enantioenriched α,β-aziridinylsilane (see Supporting Information).
  • 32
    • 18244396454 scopus 로고    scopus 로고
    • note
    • 3SnCl.
  • 33
    • 18244379140 scopus 로고    scopus 로고
    • note
    • 2 resulted in contamination with undesired tin byproducts.
  • 34
    • 18244390817 scopus 로고    scopus 로고
    • note
    • 3OD after 5 min gave a lower yield of aziridine 6.
  • 35
    • 0001318042 scopus 로고    scopus 로고
    • Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
    • (1996) Chem. Rev. , vol.96 , pp. 3303-3325
    • Satoh, T.1
  • 36
    • 18244403373 scopus 로고    scopus 로고
    • note
    • We suspect that the modest yields in these cases are due to the other diastereomer being formed competitively, but undergoing degradation via N- to O- Bus migration.
  • 38
    • 18244385848 scopus 로고    scopus 로고
    • CCDC 259770 available at http://www.ccdc.cam.ac.uk.
  • 41
    • 18244405156 scopus 로고    scopus 로고
    • note
    • Attempted trapping with other electrophiles, such as allyl bromide, BnBr, BuOTf, and MeI, has so far been unsuccessful.
  • 44
    • 18244395178 scopus 로고    scopus 로고
    • note
    • 2, or Florisil for the aziridinyl aldehyde in entry 8) gave the substituted aziridine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.