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Volumn 71, Issue 20, 2006, Pages 7888-7891

Stereoselective synthesis of (E)-mannosylidene derivatives using the Wittig reaction

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; GLUCOSE; ISOMERS; NITROGEN COMPOUNDS; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

EID: 33749133196     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061178s     Document Type: Article
Times cited : (14)

References (16)
  • 8
    • 33749131574 scopus 로고    scopus 로고
    • note
    • This might be caused by basic contaminants rather than the basicity of the ylide itself; Xie has noted in ref 3b that epimerizations of other lactones occurred only when ylides were not adequately washed free of base.
  • 10
    • 0001671643 scopus 로고
    • Isomerization of enol ethers with electron-withdrawing substituents occurs relatively easily, and 2-(ethoxycarbonylmethylene)tetrahydropyran isomerizes spontaneously on standing: (a) Sauvé, G.; Deslongchamps, P. Synth. Commun. 1985, 15, 201-212.
    • (1985) Synth. Commun. , vol.15 , pp. 201-212
    • Sauvé, G.1    Deslongchamps, P.2
  • 11
    • 0013591272 scopus 로고
    • We found that (E)-8d and (Z)-8d did not interconvert when heated in toluene (111°C, 24 h). Wittig reactions on cyclic anhydrides often proceed via acyclic acylphosphorane intermediates to yield enol lactone products of E-geometry, even though the (Z)-isomers are more stable: (b) Abell, A. D.; Massy-Westropp, R. A. Aust. J. Chem. 1982, 35, 2077-2087.
    • (1982) Aust. J. Chem. , vol.35 , pp. 2077-2087
    • Abell, A.D.1    Massy-Westropp, R.A.2
  • 12
    • 0035857259 scopus 로고    scopus 로고
    • Bérces, A.; Whitfield, D. M.; Nukada, T. Tetrahedron 2001, 57, 477-491. The conformation of a six-membered ring can be expressed in spherical polar coordinates such that d indicates the amount of puckering; θ = 0 or 180° corresponds to a chair; θ = 90°, φ = 60n (where n = 0, 1, 2, ...) corresponds to a boat, and θ = 90°, φ = 60(n + 0.5) corresponds to a twist-boat. (Z)-8d gives d = 0.96; φ = 74°; θ = 88°.
    • (2001) Tetrahedron , vol.57 , pp. 477-491
    • Bérces, A.1    Whitfield, D.M.2    Nukada, T.3
  • 13
    • 33749119217 scopus 로고    scopus 로고
    • note
    • J values for (Z)-8b are available from ref 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.