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Volumn 53, Issue 48, 1997, Pages 16597-16606

Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKANONE;

EID: 0030827536     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01039-9     Document Type: Conference Paper
Times cited : (20)

References (41)
  • 2
    • 85013550214 scopus 로고
    • H. Suschitzky and E. F. V. Scriven, Eds.; Pergamon: New York
    • Padwa, A.; Murphree, S. S. In Progress in Heterocyclic Chemistry; H. Suschitzky and E. F. V. Scriven, Eds.; Pergamon: New York, 1994; Vol. 6; pp 56-73.
    • (1994) Progress in Heterocyclic Chemistry , vol.6 , pp. 56-73
    • Padwa, A.1    Murphree, S.S.2
  • 8
    • 0000475062 scopus 로고
    • Similar reactions have been observed for alkylidenesiliranes: Saso, H.; Ando, W.; Ueno, K. Tetrahedron 1989, 45, 1929-1940.
    • (1989) Tetrahedron , vol.45 , pp. 1929-1940
    • Saso, H.1    Ando, W.2    Ueno, K.3
  • 24
    • 0004266987 scopus 로고
    • Wiley: New York
    • For the related carbon systems, γ-hydroxyaldehydes preferentially adopt the tetrahydrofuran hemiacetal form: Stoddart, J. F. Stereochemistry of Carbohydrates; Wiley: New York, 1971, pp 29-31.
    • (1971) Stereochemistry of Carbohydrates , pp. 29-31
    • Stoddart, J.F.1
  • 25
    • 0030039487 scopus 로고    scopus 로고
    • Hoveyda has invoked the interconversion of oxasilacyclopentane hemiacetals and β-siloxyaldehydes in the conversion of spirocyclic siloxanes to tetrahydropyran hemiacetals: Young, D. G. J.; Hale, M. R.; Hoveyda, A. H. Tetrahedron Lett. 1996, 37, 827-830.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 827-830
    • Young, D.G.J.1    Hale, M.R.2    Hoveyda, A.H.3
  • 27
    • 69449100070 scopus 로고
    • Control experiments using both anomers of the methyl acetal corresponding to 5 indicate that an oxonium ion is a reactive intermediate. For a discussion of oxonium intermediates as intermediates in nucleophilic substitution reactions of acetals, see: Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1994, 116 7915-7916.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7915-7916
    • Sammakia, T.1    Smith, R.S.2
  • 28
    • 0026529460 scopus 로고
    • Hoveyda has pioneered the use of oxasilacyclopentanes to control the stereochemistry of reactions on exocyclic substituents: (a) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643-1645.
    • (1992) J. Org. Chem. , vol.57 , pp. 1643-1645
    • Hale, M.R.1    Hoveyda, A.H.2
  • 30
    • 0001210176 scopus 로고
    • Stereoselective nucleophilic addition to dioxasilacyclohexane carbocations was used for the formation of carbon-carbon bonds; the stereochemistry was controlled by stereoelectronic effects: Davis, A. P.; Hegarty, S. C. J. Am. Chem. Soc. 1992, 114, 2745-2746.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2745-2746
    • Davis, A.P.1    Hegarty, S.C.2
  • 37
    • 0343365153 scopus 로고    scopus 로고
    • Hydrolysis of 24 with acid regenerated 21, indicating that epimerization did not occur during the formation of the hydrazone
    • Hydrolysis of 24 with acid regenerated 21, indicating that epimerization did not occur during the formation of the hydrazone.
  • 38
    • 0001595526 scopus 로고
    • Intramolecular additions of silylenol ethers to aldehydes in the presence of Lewis acids exhibit only a modest preference for antiperiplanar transition states: Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707-709.
    • (1994) J. Org. Chem. , vol.59 , pp. 707-709
    • Denmark, S.E.1    Lee, W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.