메뉴 건너뛰기




Volumn 50, Issue 15, 1994, Pages 4557-4574

Catalytic asymmetric Diels-Alder reactions of 2-pyrone derivatives

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE;

EID: 0028302406     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)89387-X     Document Type: Article
Times cited : (78)

References (44)
  • 11
    • 84986401444 scopus 로고
    • Herstellung substituierter 1,6-Methano[10]annulene durch Cycloadditionsreaktionen des 1H-Cyclopropabenzols
    • For the use of perchlorinated thiophene dioxide as a 2-pyrone analogue, see
    • (1989) Helvetica Chimica Acta , vol.72 , pp. 1311
    • Neidlein1    Kohl2    Kramer3
  • 14
    • 84921175882 scopus 로고    scopus 로고
    • Careful temperature control must be excercised in this case to avoid the competing intramolecular Diels-Alder reaction.
  • 16
    • 84921175881 scopus 로고    scopus 로고
    • Markó, I.E.; Swarbrick, T.M. unpublished reports.
  • 18
    • 85005707110 scopus 로고
    • Microbial Oxidation of Chloroaromatics in the Enantiocontrolled Synthesis of Cyclitols: (-)-Dihydroconduritol C
    • (1990) Synlett , pp. 309
    • Hudlicky1    Price2    Luna3    Andersen4
  • 19
    • 84987474619 scopus 로고
    • Enantioselective Syntheses of Conduramines from Benzene by Microbial Oxidation, Enzymatic Asymmetrization and Resolution in Organic Media
    • (1992) Synlett , pp. 388
    • Johnson1    Ple2    Su3    Heeg4    Adams5
  • 20
    • 0342810942 scopus 로고
    • PREPARATION OF CHIRAL, NONRACEMIC Y-LACTONES BY ENZYMECATALYZED OXIDATION OF meso-DIOLS: ( + )-(1R,6S)-8-OXABICYCLO[4.3.0]NONAN-7-ONE
    • For leading references on the N.I.H. shift, see
    • (1985) Organic Syntheses , vol.63 , pp. 10
    • Jones1    Jakovac2
  • 24
    • 84921175880 scopus 로고    scopus 로고
    • This excellent endo-selectivity contrasts with the moderate levels of stereocontrol observed in the cycloadditions of the related 5-carbomethoxy-2-pyrone (5-CMP) with enol ethers (reference 12).
  • 26
    • 84986437114 scopus 로고
    • Peri-selective photocycloadditions of methyl 2-pyrone-5-carboxylate with unsaturated cyclic ethers
    • We are grateful to Prof. Shimo for sending us preprints of his work.and references cited therein
    • (1992) Journal of Heterocyclic Chemistry , vol.29 , pp. 199
    • Shimo1    Iwakiri2    Somekawa3
  • 27
    • 84921175879 scopus 로고    scopus 로고
    • Markó, I.E.; Swarbrick, T.M. unpublished reports.
  • 28
    • 0010077452 scopus 로고
    • For a leading review on the role of lanthanides in organic synthesis, see
    • (1992) Chem. Rev. , vol.92 , pp. 29
    • Molander1
  • 35
    • 84921175878 scopus 로고    scopus 로고
    • The difference in rate of reaction between coordinated 3-CMP and coordinated 9d suggests that a different mode of binding of the Lewis acid is involved in the latter case. It is important to realise that too strong a coordination of 3-CMP results in deactivation of the 2-pyrone towards dienophiles, owing to the formation of the pyrillium salt. We are very grateful to Professor G. Helmchen for extensive discussion of this reaction mechanism.
  • 38
    • 84921175877 scopus 로고    scopus 로고
    • 3 coordinates too strongly to 3-CMP, forming the unreactive pyrillium form. By adding an alcohol and displacing one or two triflate ligands, the Lewis acidity of the lanthanide is lowered and IEDDA reaction ensues.
  • 43
    • 84921932224 scopus 로고
    • A Convenient Synthesis of Aryl Vinyl Ethers by Use of Tetra-n-butylammonium Hydrogen Sulfate
    • (1979) Synthesis , pp. 688
    • Mizuno1    Kimura2    Otsuji3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.