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Volumn 79, Issue C, 2009, Pages 353-358

Stereoselective synthesis of 5-substituted 2-allyl-3-oxotetrahydrofuran-2-carboxylates using rhodium(II)-catalyzed oxonium ylide formation-[2,3] shift

Author keywords

3 Oxotetrahydrofuran; 5 Allyloxy 2 diazo 3 keto Ester; Dirhodium(II) Tetraacetate; Heliespirone; Oxonium Ylide Formation 2,3 Shift

Indexed keywords


EID: 67651089980     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(D)22     Document Type: Article
Times cited : (8)

References (37)
  • 6
    • 0041801189 scopus 로고    scopus 로고
    • Treatment of methyl 5-tert-butyldimethylsilyloxy-2-diazo-3-oxoheptanoate with Rh(II) catalyst selectively afforded the C-H insertion product. See
    • Treatment of methyl 5-tert-butyldimethylsilyloxy-2-diazo-3-oxoheptanoate with Rh(II) catalyst selectively afforded the C-H insertion product. See. Yakura T., Yamada S., Ueki A., and Ikeda M. Synlett (1997) 185
    • (1997) Synlett , pp. 185
    • Yakura, T.1    Yamada, S.2    Ueki, A.3    Ikeda, M.4
  • 8
    • 0031827988 scopus 로고    scopus 로고
    • Chemoselectivity (C-H insertion reaction vs. oxonium ylide formation) in Rh(II)-catalyzed reaction of 5,6-dioxygenated 2-diazo-3-oxohexanoates was controlled by their O-protecting groups. See
    • Chemoselectivity (C-H insertion reaction vs. oxonium ylide formation) in Rh(II)-catalyzed reaction of 5,6-dioxygenated 2-diazo-3-oxohexanoates was controlled by their O-protecting groups. See. Yakura T., Ueki A., Morioka Y., Kurata T., Tanaka K., and Ikeda M. Chem. Pharm. Bull. 46 (1997) 1182
    • (1997) Chem. Pharm. Bull. , vol.46 , pp. 1182
    • Yakura, T.1    Ueki, A.2    Morioka, Y.3    Kurata, T.4    Tanaka, K.5    Ikeda, M.6
  • 32
    • 67651107076 scopus 로고    scopus 로고
    • note
    • Treatment of 5 with 2,2-dimethoxypropane in the presence of camphorsulfonic acid (CSA) gave the corresponding acetonide within 10 min, although a similar reaction of 6 did not proceed after 24 h. {A figure is presented}
  • 35
    • 67651126248 scopus 로고    scopus 로고
    • note
    • 2 (20 mL) was stirred at rt. After 1 was consumed completely, as indicated by TLC, the mixture was concentrated and purified using column chromatography on silica gel to give pure 2. All new compounds gave satisfactory spectroscopic data.
  • 36
    • 67651126247 scopus 로고    scopus 로고
    • note
    • 15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.