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Volumn 74, Issue 4, 2009, Pages 1531-1540

Gosteli-claisen rearrangement: Substrate synthesis, simple diastereoselectivity, and kinetic studies

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL VINYL ETHERS; CLAISEN REARRANGEMENTS; DIASTEREO SELECTIVITIES; KINETIC STUDIES; RATE EFFECTS; SIGMATROPIC REARRANGEMENTS; TRANSITION STATE;

EID: 64349087921     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802303m     Document Type: Article
Times cited : (37)

References (94)
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    • (b) Claisen, L. Chem. Ber. 1912, 45, 3157-3167.
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    • For selected review articles, see: a
    • For selected review articles, see: (a) Tarbell, D. S. Chem. Rev. 1940, 27, 495-546.
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    • For the chiral Lewis acid catalyzed Gosteli-Claisen rearrangement, see: a
    • For the chiral Lewis acid catalyzed Gosteli-Claisen rearrangement, see: (a) Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem., Int. Ed. 2001, 40, 4700-4703.
    • (2001) Angew. Chem., Int. Ed , vol.40 , pp. 4700-4703
    • Abraham, L.1    Czerwonka, R.2    Hiersemann, M.3
  • 80
    • 20444482486 scopus 로고    scopus 로고
    • To avoid over-reduction and E/Z isomerization, it was pivotal to monitor the progress of the hydrogenation by GC
    • Balduzzi, S.; Brook, M. A.; McGlinchey, M. J Organometallics 2005, 24, 2617-2627, To avoid over-reduction and E/Z isomerization, it was pivotal to monitor the progress of the hydrogenation by GC.
    • (2005) Organometallics , vol.24 , pp. 2617-2627
    • Balduzzi, S.1    Brook, M.A.2    McGlinchey, M.J.3
  • 81
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    • 4, i-PrOH, reflux) were unsuccessful.
    • 4, i-PrOH, reflux) were unsuccessful.
  • 82
    • 64349104849 scopus 로고    scopus 로고
    • Isolated as inseparable mixtures of diastereomers. The relative configuration of the major and minor diastereomer was not assigned
    • Isolated as inseparable mixtures of diastereomers. The relative configuration of the major and minor diastereomer was not assigned.
  • 83
    • 64349113083 scopus 로고    scopus 로고
    • Care must be taken during the purification and isolation of the allyl vinyl ether 1a and 1b because of their volatility at reduced pressure.
    • Care must be taken during the purification and isolation of the allyl vinyl ether 1a and 1b because of their volatility at reduced pressure.
  • 88
    • 0000518212 scopus 로고    scopus 로고
    • A 25-fold rate acceleration in TFE compared to benzene has been experimentally determined for a Claisen rearrangement, see: Brandes, E.; Grieco, P. A.; Gajewski, J. J. J. Org. Chem. 1989, 54, 515-516.
    • A 25-fold rate acceleration in TFE compared to benzene has been experimentally determined for a Claisen rearrangement, see: Brandes, E.; Grieco, P. A.; Gajewski, J. J. J. Org. Chem. 1989, 54, 515-516.
  • 89
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    • Strassner and co-workers have calculated a gas-phase ΔG† for (Z)-1c of 27.4kcal/mol at the DFG B3LYP/6-311++G** level of theory; see ref 17. This value is in very good agreement with our experimentally determined values in benzene-d6(28.1 kcal/mol) or DCE 27.9 kcal/mol
    • 6(28.1 kcal/mol) or DCE (27.9 kcal/mol).
  • 91
    • 64349096315 scopus 로고    scopus 로고
    • 2)//B3LYP/ 6-31G* level of theory; see: Ozturk, C.; Balta, B.; Aviyente, V.; Vincent, M. A.; Hillier, I. H. J. Org. Chem. 2008, 73, 4800-4809.
    • 2)//B3LYP/ 6-31G* level of theory; see: Ozturk, C.; Balta, B.; Aviyente, V.; Vincent, M. A.; Hillier, I. H. J. Org. Chem. 2008, 73, 4800-4809.
  • 92
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    • For an insightful discussion on this topic, see
    • For an insightful discussion on this topic, see: Gajewski, J. J. Acc. Chem. Res. 1997, 30, 219-225.
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    • Gajewski, J.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.