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Volumn 3, Issue 22, 2001, Pages 3591-3593

Improved E-selectivity in the Wittig reaction of stabilized ylides with α-alkoxyaldehydes and sugar lactols

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; MONOSACCHARIDE; PHOSPHORANE DERIVATIVE;

EID: 0035512706     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016729+     Document Type: Article
Times cited : (64)

References (30)
  • 3
    • 0043229399 scopus 로고
    • The basis for the effect, which has been known for some time, of carboxylic acids upon Wittig reactions of stabilized ylides is not well understood. See: (a) Buchanan, J. G.; Edgar, A. R.; Power, M. J.; Theaker, P. D. Carbohydr. Res. 1974, 38, C22-C24.
    • (1974) Carbohydr. Res. , vol.38
    • Buchanan, J.G.1    Edgar, A.R.2    Power, M.J.3    Theaker, P.D.4
  • 9
    • 0042728111 scopus 로고    scopus 로고
    • note
    • 1H NMR. All yields are of the pure E/Z mixture after chromatography.
  • 17
    • 0041726893 scopus 로고    scopus 로고
    • note
    • 2 was successively evaporated. This solution was then added to a stirred solution of 3 (7.60 g, 40.0 mmol) and benzoic acid (976 mg, 8.00 mmol) in toluene (200 mL) at 90 °C. After 10 min the solvent was evaporated, and the residue was purified by flash chromatography with hexanes/EtOAc (1:1 → 1:2) to give 7.71 g (78%) of 4 (E/Z = 91:9) as a pale yellow solid.
  • 18
    • 0042227212 scopus 로고    scopus 로고
    • note
    • 1H NMR. All yields are of the pure E/Z mixture after chromatography.
  • 21
    • 1542442610 scopus 로고
    • The reaction of 6 with 5a in MeOH provides 7 in 81% yield (E/Z = 20:80), see ref 2
    • Bernardi, A.; Cardani, S.; Scolastico, C.; Villa, R. Tetrahedron 1988, 44, 491-502. The reaction of 6 with 5a in MeOH provides 7 in 81% yield (E/Z = 20:80), see ref 2.
    • (1988) Tetrahedron , vol.44 , pp. 491-502
    • Bernardi, A.1    Cardani, S.2    Scolastico, C.3    Villa, R.4
  • 23
    • 33751386344 scopus 로고
    • Prepared in one step (44%) from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 3586-3588.
    • (1993) J. Org. Chem. , vol.58 , pp. 3586-3588
    • Wu, W.-L.1    Wu, Y.-L.2
  • 24
    • 0021106325 scopus 로고
    • The reaction of 10 with 5a in MeOH provides 11 in 70% yield (E/Z= 12:88), see ref 2
    • Horton, D.; Machinami, T.; Takagi, Y. Carbohydr. Res. 1983, 121, 135-161. The reaction of 10 with 5a in MeOH provides 11 in 70% yield (E/Z= 12:88), see ref 2.
    • (1983) Carbohydr. Res. , vol.121 , pp. 135-161
    • Horton, D.1    Machinami, T.2    Takagi, Y.3
  • 25
    • 24444453551 scopus 로고
    • Prepared in two steps (68%) from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose: Kovár, J.; Baer, H. H. Can. J. Chem. 1973, 51, 1801-1811.
    • (1973) Can. J. Chem. , vol.51 , pp. 1801-1811
    • Kovár, J.1    Baer, H.H.2
  • 26
    • 0000401162 scopus 로고
    • The reaction of 12 with 5a in MeOH provides 13 in unknown yield (E/Z = 8:92)
    • Tronchet, J. M. J.; Gentile, B. Helv. Chim. Acta 1979, 62, 2091-2098. The reaction of 12 with 5a in MeOH provides 13 in unknown yield (E/Z = 8:92).
    • (1979) Helv. Chim. Acta , vol.62 , pp. 2091-2098
    • Tronchet, J.M.J.1    Gentile, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.