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Volumn 45, Issue 28, 2004, Pages 5359-5361

Diastereoselectivity in the epoxidation of γ-hydroxy α,β-unsaturated esters: Temperature and solvent effect

Author keywords

Diastereoselective epoxidation; Solvent effect; Temperature influence; Unsaturated esters

Indexed keywords

ESTER DERIVATIVE; HYDROXYL GROUP; LITHIUM DERIVATIVE; LITHIUM TERT BUTYLPEROXIDE; PEROXIDE; SOLVENT; UNCLASSIFIED DRUG;

EID: 2942695699     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.080     Document Type: Article
Times cited : (19)

References (22)
  • 13
    • 0001562620 scopus 로고
    • For stereoselective Michael reactions of γ-alkoxy α,β-unsaturated esters see:
    • For stereoselective Michael reactions of γ-alkoxy α, β-unsaturated esters see: Yamamoto Y., Chounan Y., Nishii S., Ibuka T., Kitahara H. J. Am. Chem. Soc. 114:1992;7652-7660
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7652-7660
    • Yamamoto, Y.1    Chounan, Y.2    Nishii, S.3    Ibuka, T.4    Kitahara, H.5
  • 15
    • 2942683527 scopus 로고    scopus 로고
    • Although the reactions in Scheme 2 appear in the literature, they have been optimised so as to provide an efficient way of making aldehyde 5
  • 18
    • 25044439976 scopus 로고
    • Distillation over potassium bisulfate of the crude is necessary to convert a nondesired product resulting from ethanol incorporation into the desired alkene 4
    • Distillation over potassium bisulfate of the crude is necessary to convert a nondesired product resulting from ethanol incorporation into the desired alkene 4: See: Fariña F., Victory P. Tetrahedron Lett. 38:1969;3219-3222
    • (1969) Tetrahedron Lett. , vol.38 , pp. 3219-3222
    • Fariña, F.1    Victory, P.2
  • 20
    • 0000439467 scopus 로고    scopus 로고
    • When we used n-BuLi partial transesterification of the epoxy ethyl ester was observed, this must be due to the formation of n-BuOLi from oxidation of n-BuLi by TBPLi (see: ) or probably already present in the n-BuLi. If EtLi is used, the ester is not affected
    • When we used n-BuLi partial transesterification of the epoxy ethyl ester was observed, this must be due to the formation of n-BuOLi from oxidation of n-BuLi by TBPLi (see: Boche G., Mbus K., Harms K., Lohrenz J.C.W., Marsch M. Chem. Eur. J. 2:1996;604-607. ) or probably already present in the n-BuLi. If EtLi is used, the ester is not affected
    • (1996) Chem. Eur. J. , vol.2 , pp. 604-607
    • Boche, G.1    Mbus, K.2    Harms, K.3    Lohrenz, J.C.W.4    Marsch, M.5
  • 22
    • 2942668584 scopus 로고    scopus 로고
    • note
    • Modelling of the lactones give as the closest distance between the methyl and H-1: 3 Å for syn-anti lactone (possible NOE) and 4.2 Å for the syn-syn one (no possible NOE)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.