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Volumn 125, Issue 41, 2003, Pages 12502-12508

Chiral Ru-based complexes for asymmetric olefin metathesis: Enhancement of catalyst activity through steric and electronic modifications

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METATHESIS;

EID: 0141885397     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0302228     Document Type: Article
Times cited : (265)

References (60)
  • 38
    • 0035807528 scopus 로고    scopus 로고
    • For an alternative class of chiral Ru catalysts for olefin metathesis, see: Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228.
    • (2001) Org. Lett. , vol.3 , pp. 3225-3228
    • Seiders, T.J.1    Ward, D.W.2    Grubbs, R.H.3
  • 39
    • 0035793845 scopus 로고    scopus 로고
    • As an example, the reaction shown in Tables 1-2 affords only polymerization products in the presence of chiral Mo-based complexes. For an overview of Mo-catalyzed enantioselective olefin metathesis, see: (a) Hoveyda, A. H.; Schrock, R. R. Chem., A Eur. J. 2001, 7, 945-950.
    • (2001) Chem., A Eur. J. , vol.7 , pp. 945-950
    • Hoveyda, A.H.1    Schrock, R.R.2
  • 42
    • 0141893903 scopus 로고    scopus 로고
    • note
    • 3 instead of OMe) could not be prepared due to susceptibility of the requisite styrene to undergo rapid polymerization.
  • 43
    • 0141928460 scopus 로고    scopus 로고
    • note
    • These are the same enantioselectivities observed with parent complex 3. In our previous report (ref 9), enantioselectivity values for non-UV-active products from reactions of 10 with 1-heptene and vinylcyclohexane were measured by HPLC/ELSD methods to be >98% ee. Subsequent investigations indicated that ELSD methods are unreliable in measuring ee values (of at least this class of compounds). Alternative approaches led us to determine subsequently that the above reactions proceed in 80-82% ee. The remaining enantioselectivities in ref 9 are correct as initially reported.
  • 44
    • 0141928461 scopus 로고    scopus 로고
    • note
    • Reaction in air with 5 mol % 3d proceeded to 50% conv after one h, presumably due to instability of the more reactive and sensitive catalyst.
  • 45
    • 0141997609 scopus 로고    scopus 로고
    • note
    • 1 bond length is 2.252 Å in 3 and for 3d the two molecules in the unit cell show bond lengths of 2.267 and 2.294 Å, respectively.
  • 46
    • 0141893904 scopus 로고    scopus 로고
    • note
    • 2 styrene ether.
  • 47
    • 0141928459 scopus 로고    scopus 로고
    • note
    • 3-bearing Ru carbene. Moreover, recovery of the fluorinated Ru catalysts, including 3e, is more cumbersome than the derived nonfluorinated analogues.
  • 59
    • 0001567886 scopus 로고    scopus 로고
    • Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley-VCH: Weinheim
    • For a discussion of the concept of "catalyst generality", see: Hoveyda, A. H. In Handbook of Combinatorial Chemistry Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley-VCH: Weinheim; 2002; pp 991-1016.
    • (2002) Handbook of Combinatorial Chemistry , pp. 991-1016
    • Hoveyda, A.H.1
  • 60
    • 0141893900 scopus 로고    scopus 로고
    • note
    • The reaction of triene 37 in THF affords 38 in 65% ee; subsequent brief solvent screening proved dichloroethane to be a superior medium.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.