메뉴 건너뛰기




Volumn 65, Issue 46, 2009, Pages 9637-9646

Trisubstituted cyclooctene synthesis at the limits of relay ring-closing metathesis: a racemic difluorinated analogue of fucose

Author keywords

2,3 Wittig rearrangement; Effective molarity; Fluorinated building block; Fucose analogue; Mechanism; Medium ring; Metallated enol acetal; Mimetics; Monosaccharide; Relay ring closing metathesis; Ring closing metathesis; Trisubstituted alkene

Indexed keywords

CYCLOOCTANE DERIVATIVE; FUCOSE;

EID: 70349729948     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.076     Document Type: Article
Times cited : (9)

References (60)
  • 1
    • 70349753093 scopus 로고    scopus 로고
    • For recent reviews, see
    • For recent reviews, see:
  • 11
    • 70349740922 scopus 로고    scopus 로고
    • Examples which fail to deliver cyclooctanes
    • Examples which fail to deliver cyclooctanes:
  • 15
    • 0030750030 scopus 로고    scopus 로고
    • For an example in which a bulky (tributylstannyl) substituent ensures success, see
    • For an example in which a bulky (tributylstannyl) substituent ensures success, see. Linderman R.J., Siedlecki J., O'Neill S.A., and Sun H. J. Am. Chem. Soc. 119 (1997) 6919
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 6919
    • Linderman, R.J.1    Siedlecki, J.2    O'Neill, S.A.3    Sun, H.4
  • 21
    • 33748544300 scopus 로고    scopus 로고
    • For a review of medium ring synthesis by RCM, see
    • For a review of medium ring synthesis by RCM, see. Michaut A., and Rodriguez J. Angew. Chem., Int. Ed. 45 (2006) 5740
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 5740
    • Michaut, A.1    Rodriguez, J.2
  • 22
    • 70349746936 scopus 로고    scopus 로고
    • For recent examples of eight-membered ring formation, see
    • For recent examples of eight-membered ring formation, see:
  • 26
    • 12344273571 scopus 로고    scopus 로고
    • For recent syntheses of trisubstituted cyclooctenones by RCM, see
    • For recent syntheses of trisubstituted cyclooctenones by RCM, see. Michalak M., and Wicha J. Tetrahedron Lett. 46 (2005) 1149
    • (2005) Tetrahedron Lett. , vol.46 , pp. 1149
    • Michalak, M.1    Wicha, J.2
  • 34
    • 38949085170 scopus 로고    scopus 로고
    • In this extremely useful recent review, Grela and co-workers suggest a series of measures, which can be used to test the feasibility of an RCM reaction rapidly; reaction in hot toluene is recommended for sluggish reactions
    • Bieniek M., Michrowska A., Usanov D.L., and Grela K. Chem.-Eur. J. 14 (2008) 806 In this extremely useful recent review, Grela and co-workers suggest a series of measures, which can be used to test the feasibility of an RCM reaction rapidly; reaction in hot toluene is recommended for sluggish reactions
    • (2008) Chem.-Eur. J. , vol.14 , pp. 806
    • Bieniek, M.1    Michrowska, A.2    Usanov, D.L.3    Grela, K.4
  • 36
    • 70349755569 scopus 로고    scopus 로고
    • For recent applications of RRCM, see
    • For recent applications of RRCM, see:
  • 40
    • 61849093212 scopus 로고    scopus 로고
    • In this recent example, RRCM fails to deliver as slow cyclisation erodes the advantage of an enhanced rate of initiation
    • Tannert R., Hu T.S., Arndt H.D., and Waldmann H. Chem. Commun. (2009) 1493 In this recent example, RRCM fails to deliver as slow cyclisation erodes the advantage of an enhanced rate of initiation
    • (2009) Chem. Commun. , pp. 1493
    • Tannert, R.1    Hu, T.S.2    Arndt, H.D.3    Waldmann, H.4
  • 45
    • 34249315416 scopus 로고    scopus 로고
    • identifies the importance of dispersive interactions in Grubbs second generation alkylidenes
    • Zhao Y., and Truhlar D.G. Org. Lett. 9 (2007) 1967 identifies the importance of dispersive interactions in Grubbs second generation alkylidenes
    • (2007) Org. Lett. , vol.9 , pp. 1967
    • Zhao, Y.1    Truhlar, D.G.2
  • 46
    • 34548569064 scopus 로고    scopus 로고
    • highlights the shortcomings of B3LYP in producing reliable reaction energies
    • Piacenza M., Hyla-Kryspin I., and Grimme S. J. Comput. Chem. 28 (2007) 2275 highlights the shortcomings of B3LYP in producing reliable reaction energies
    • (2007) J. Comput. Chem. , vol.28 , pp. 2275
    • Piacenza, M.1    Hyla-Kryspin, I.2    Grimme, S.3
  • 47
    • 56849123754 scopus 로고    scopus 로고
    • shows how the M06 functionals achieve good results for cross-metathesis
    • Benitez D., Tkatchouk E., and Goddard W.A. Chem. Commun. (2008) 6194 shows how the M06 functionals achieve good results for cross-metathesis
    • (2008) Chem. Commun. , pp. 6194
    • Benitez, D.1    Tkatchouk, E.2    Goddard, W.A.3
  • 49
    • 36849028500 scopus 로고    scopus 로고
    • Wavefunction, Irvine, CA
    • Spartan'06 (2006), Wavefunction, Irvine, CA
    • (2006) Spartan'06
  • 52
    • 39549084947 scopus 로고    scopus 로고
    • The data used in these plots were extracted manually from graphics in the supplementary information of
    • The data used in these plots were extracted manually from graphics in the supplementary information of. Vougioukalakis G.C., and Grubbs R.H. J. Am. Chem. Soc. 130 (2008) 2234
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2234
    • Vougioukalakis, G.C.1    Grubbs, R.H.2
  • 55
    • 70349750123 scopus 로고    scopus 로고
    • For reports of alkylidene transfer accelerated by their presence of an allylic hydroxyl group, see
    • For reports of alkylidene transfer accelerated by their presence of an allylic hydroxyl group, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.