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Volumn , Issue 13, 2006, Pages 2079-2082

Direct preparation of Z-1,3-enyne systems with a TMS-propargylic sulfone: Application of a one-pot Julia olefination

Author keywords

Aldehydes; Enynes; Natural products; Olefination; Propargylic sulfones

Indexed keywords

SULFONE DERIVATIVE;

EID: 33748276427     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948196     Document Type: Article
Times cited : (23)

References (38)
  • 27
    • 33748285856 scopus 로고    scopus 로고
    • note
    • Premetallated conditions: base added to sulfone, then aldehyde added.
  • 28
    • 33748274581 scopus 로고    scopus 로고
    • note
    • Barbier conditions: base added to the mixture of sulfone and aldehyde.
  • 29
    • 33748264626 scopus 로고    scopus 로고
    • note
    • Pent-2-ynyl BT-sulfone, reacting with benzaldehyde according to method A, afforded the corresponding enyne in only 18% yield but with 94:6 Z/E ratio.
  • 30
    • 0037087785 scopus 로고    scopus 로고
    • For other examples with high cis-selectivity during the one-pot Julia olefination of allyl benzothiazolyl sulfones with α,β-unsaturated aldehydes, see: (a) Furuichi, N.; Hara, H.; Osaki, T.; Mori, H.; Katsumura, S. Angew. Chem. Int. Ed. 2002, 41, 1023.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1023
    • Furuichi, N.1    Hara, H.2    Osaki, T.3    Mori, H.4    Katsumura, S.5
  • 32
    • 33748286257 scopus 로고    scopus 로고
    • Ref. 13
    • Ref. 13.
  • 36
    • 33748282215 scopus 로고    scopus 로고
    • manuscript in preparation
    • Preparation of aldehyde 8f, starting from the alcohol 9 (Scheme 3). Alcohol 9 was prepared according to: Bonini, C.; Chiummiento, L.; Videtta, V.; Colobert, F.; Solladié, G., manuscript in preparation. (Diagram presented) Scheme 3
    • Bonini, C.1    Chiummiento, L.2    Videtta, V.3    Colobert, F.4    Solladié, G.5
  • 37
    • 33748277855 scopus 로고    scopus 로고
    • note
    • No β-elimination product was observed for aldehyde 8e. Moreover, the optical rotation for the unreacted aldehyde 8f shows the same the value of the starting aldehyde, thus indicating that no epimerization reaction occurs.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.