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Volumn 9, Issue 11, 2007, Pages 2087-2090

Acidity-directed synthesis of substituted γ-Butyrolactones from aliphatic aldehydes

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EID: 34250623275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0705806     Document Type: Article
Times cited : (49)

References (43)
  • 6
    • 33748588238 scopus 로고
    • For a review on α-methylene-β-butyrolactones, see
    • (b) For a review on α-methylene-β-butyrolactones, see: Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. 1985, 24, 110.
    • (1985) Angew. Chem., Int. Ed , vol.24 , pp. 110
    • Hoffmann, H.M.R.1    Rabe, J.2
  • 7
    • 12344281907 scopus 로고    scopus 로고
    • For a review on lactones as generic inhibitors of enzymes, see
    • (c) For a review on lactones as generic inhibitors of enzymes, see: Konaklieva, M. I.; Plotkin, B. J. MiniRev. Med. Chem. 2005, 5, 73.
    • (2005) MiniRev. Med. Chem , vol.5 , pp. 73
    • Konaklieva, M.I.1    Plotkin, B.J.2
  • 20
    • 0037009989 scopus 로고    scopus 로고
    • For earlier reports on Lewis or Bronsted acid-catalyzed crotylboration, see: a
    • For earlier reports on Lewis or Bronsted acid-catalyzed crotylboration, see: (a) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 11586
    • Kennedy, J.W.J.1    Hall, D.G.2
  • 24
    • 84981828672 scopus 로고    scopus 로고
    • Following the Cahn - Ingold - Prelog priority rules, the parent Z- and E-crotylboronates become E- and Z-, respectively (E-1 and E-5, and Z-1 and Z-5), when substituted with a COOMe group. Cahn, R. S.; Ingold, C.; Prelog, V. Angen: Chem., Int. Ed. Engl. 1966, 5, 385.
    • (a) Following the Cahn - Ingold - Prelog priority rules, the parent Z- and E-crotylboronates become E- and Z-, respectively (E-1 and E-5, and Z-1 and Z-5), when substituted with a COOMe group. Cahn, R. S.; Ingold, C.; Prelog, V. Angen: Chem., Int. Ed. Engl. 1966, 5, 385.
  • 25
    • 33947468884 scopus 로고    scopus 로고
    • It should be remembered that the parent Z- and E-crotylboronates give cis-and trans-d-methyl homoallyl alcohols, respectively, via a six-membered Zimmerman-Traxler transition state. Zimmerman, H. E, Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920
    • (b) It should be remembered that the parent Z- and E-crotylboronates give cis-and trans-d-methyl homoallyl alcohols, respectively, via a six-membered Zimmerman-Traxler transition state. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920
  • 27
    • 0034583413 scopus 로고    scopus 로고
    • For a review on the relative strengths of Lewis acids, see
    • For a review on the relative strengths of Lewis acids, see: Kobayashi, S.; Manabe, K. Pure Appl. Chem. 2000, 72, 1373.
    • (2000) Pure Appl. Chem , vol.72 , pp. 1373
    • Kobayashi, S.1    Manabe, K.2
  • 28
    • 34250662872 scopus 로고    scopus 로고
    • 3-catalyzed reaction provided a cis/trans lactone ratio of 99:1.
    • 3-catalyzed reaction provided a cis/trans lactone ratio of 99:1.
  • 33
    • 34250670920 scopus 로고    scopus 로고
    • Reagents such as E- and Z-5 have been termed higher crotylboranes, see: Brown, H. C.: Narla, G. Tetrahedron Lett. 1997, 38, 219.
    • Reagents such as E- and Z-5 have been termed "higher crotylboranes", see: Brown, H. C.: Narla, G. Tetrahedron Lett. 1997, 38, 219.
  • 34
    • 18044396543 scopus 로고    scopus 로고
    • For a discussion of a related one-pot synthesis of β- and δ-substituted homoallylic alcohols via crotylboration, see: Ramachandran, P. V, Pratihar. D, Biswas, D. Chem. Commun. 2005, 1988
    • For a discussion of a related one-pot synthesis of β- and δ-substituted homoallylic alcohols via crotylboration, see: Ramachandran, P. V.; Pratihar. D.; Biswas, D. Chem. Commun. 2005, 1988.
  • 35
    • 0032496932 scopus 로고    scopus 로고
    • For the Lewis acid-catalyzed conversion of β- to δ-substituted homoallylic alcohols, see: a
    • For the Lewis acid-catalyzed conversion of β- to δ-substituted homoallylic alcohols, see: (a) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 6609
    • Nokami, J.1    Yoshizane, K.2    Matsuura, H.3    Sumida, S.4
  • 41
    • 34250656764 scopus 로고    scopus 로고
    • Addition of a different aldehyde (2d) to the intermediate syn-8, obtained from the allylboration of 2a with E-1 under refluxing conditions, provided a mixture of lactones cu-4a and E-3d.
    • Addition of a different aldehyde (2d) to the intermediate syn-8, obtained from the allylboration of 2a with E-1 under refluxing conditions, provided a mixture of lactones cu-4a and E-3d.
  • 42
    • 34250618098 scopus 로고    scopus 로고
    • 11B NMR spectroscopy (δ 22 ppm, see the experimental details in the Supporting Information),
    • 11B NMR spectroscopy (δ 22 ppm, see the experimental details in the Supporting Information),
  • 43
    • 34250657825 scopus 로고    scopus 로고
    • The PMR spectra of the progress of the reaction for the formation of the rearranged product E-3a is also provided in the Supporting Information.
    • (b) The PMR spectra of the progress of the reaction for the formation of the rearranged product E-3a is also provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.