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Volumn 54, Issue 5-6, 1998, Pages 667-696

Synthesis and applications of optically active nitroxides

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; NITROXIDE DERIVATIVE;

EID: 0032576786     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10061-8     Document Type: Review
Times cited : (71)

References (100)
  • 8
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    • (1978) Chem. Rev. , vol.78 , pp. 37-65
    • Keana, J.F.W.1
  • 32
    • 85050296727 scopus 로고
    • 19. S = ln[(1-C)(1-ee)]/ln[(1-C)(1+ee)] where ee is the fractional enantiomeric excess and C is the fractional conversion. S values provide a clear measure of effectiveness, as ee values are very sensitive to conversion. For a discussion of kinetic resolution, see Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2
  • 34
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    • See ref. 5c and references cited therein
    • 21. See ref. 5c and references cited therein.
  • 35
    • 0010704176 scopus 로고    scopus 로고
    • See for example ref. 5a and 5b
    • 22. See for example ref. 5a and 5b.
  • 46
    • 0002352777 scopus 로고    scopus 로고
    • 31. The TEMPO-modified electrode gave kinetic resolution of 1-phenylethanol in 95% ee, S = 5.2, whereas use of a bare electrode in the presence of 4-acetylamino-TEMPO gave 3.5% ee, indicating a possible change in mechanism. (a) Kashiwagi, Y.; Yanagisawa, Y.; Kurashima, F.; Anzai, J.; Osa, T.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1996, 2745-2746.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 2745-2746
    • Kashiwagi, Y.1    Yanagisawa, Y.2    Kurashima, F.3    Anzai, J.4    Osa, T.5    Bobbitt, J.M.6
  • 51
    • 0010658546 scopus 로고    scopus 로고
    • Unpublished results from this laboratory
    • 34. Unpublished results from this laboratory.
  • 56
    • 0000711386 scopus 로고
    • 39. Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Grant, K. J.; Hodgson, P. K. G.; Thorburn, P. Heterocycles 1994, 37, 199-206. Note: the (+)-isomer of 36 was prepared starting from (-)-camphene to give (+)-carbamate 35, whereas the (-)-isomer of 36 was prepared from (-)-carbamate 35, which is commercially available from ACROS under the name Chiracamphox.®
    • (1994) Heterocycles , vol.37 , pp. 199-206
    • Banks, M.R.1    Cadogan, J.I.G.2    Gosney, I.3    Grant, K.J.4    Hodgson, P.K.G.5    Thorburn, P.6
  • 57
    • 0010667937 scopus 로고    scopus 로고
    • note
    • 40. Caution: the literature procedure for the preparation of carbamate 35 includes reaction of a chlorocarbonate with sodium azide in dichloromethane. This procedure worked without incident the first dozen times, but resulted in a massive explosion upon rotary evaporation in one instance in our laboratory. We strongly suggest substituting another solvent for dichloromethane for this step.
  • 60
    • 0010744794 scopus 로고    scopus 로고
    • See ref. 42 and references cited therein
    • 43. See ref. 42 and references cited therein.
  • 62
    • 0010705444 scopus 로고    scopus 로고
    • See ref. 46 and references cited therein
    • 45. See ref. 46 and references cited therein.
  • 64
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    • See ref. 44 and references cited therein
    • 47. See ref. 44 and references cited therein.
  • 78
  • 91
    • 0030125907 scopus 로고    scopus 로고
    • (b) For a more direct route to the racemic nitroxide, see: Puts, R. D.; Sogah, D. Y. Macromolecules 1996, 29, 3323-3325.
    • (1996) Macromolecules , vol.29 , pp. 3323-3325
    • Puts, R.D.1    Sogah, D.Y.2
  • 100
    • 0010745893 scopus 로고    scopus 로고
    • note
    • 80. Available from Aldrich Chemical Company.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.