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Volumn , Issue 14, 1998, Pages 2121-2122

Allyldiisopropylphenylsilane as a synthetic equivalent of 2-hydroxy-1,3-dipole. Stereoselective synthesis of cyclopentanols

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EID: 33748717992     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804118k     Document Type: Article
Times cited : (45)

References (39)
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    • 0001172865 scopus 로고
    • Silicon Stabilization
    • ed. B. M. Trost and I. Fleming, Pergamon, Oxford
    • For reviews: J. S. Panek, Silicon Stabilization, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 1, p. 579;
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 579
    • Panek, J.S.1
  • 14
    • 0025150608 scopus 로고
    • For the preparation of 5-membered heterocycles: H. Sugimura, Tetrahedron Lett., 1990, 31, 5909;
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5909
    • Sugimura, H.1
  • 24
    • 0001122697 scopus 로고
    • Oxidation of Carbon-Silicon Bonds
    • ed. B. M. Trost and I. Fleming, Pergamon, Oxford
    • (a) E. W. Colvin, Oxidation of Carbon-Silicon Bonds, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 7; p. 641;
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 641
    • Colvin, E.W.1
  • 27
    • 0000080248 scopus 로고    scopus 로고
    • Bulky silanes or silyl ethers which have been oxidised to alcohols: J. H. Smitrovich and K. A. Woerpel, J. Org. Chem., 1996, 61, 6044;
    • (1996) J. Org. Chem. , vol.61 , pp. 6044
    • Smitrovich, J.H.1    Woerpel, K.A.2
  • 32
    • 33748736629 scopus 로고    scopus 로고
    • note
    • 3b,3h
  • 33
    • 33748735285 scopus 로고    scopus 로고
    • note
    • Tin(IV) chloride mediated reaction gave rise to 2a in 58% yield.
  • 34
    • 33748735415 scopus 로고    scopus 로고
    • note
    • 2, hexane-ethyl acetate = 15:1, v/v) gave 2a (102 mg, 89%).
  • 35
    • 33748739715 scopus 로고    scopus 로고
    • note
    • It should be noted that allyl-tert-butyldiphenylsilane which was useful for the oxetane formation was not effective for the present cyclopentane annulation; the corresponding cycloadduct was obtained in only modest yield and oxidative cleavage of the tert-butyldiphenylsilyl group was not successful under the above conditions.
  • 37
    • 33748733680 scopus 로고    scopus 로고
    • note
    • 4N·F were 84, 0 and 0% respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.