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Volumn 71, Issue 5, 2006, Pages 2009-2013

Stereoselective synthesis of Z alkenyl halides via Julia olefination

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL HALIDES; OLEFINATION; STEREOSELECTIVE SYNTHESIS;

EID: 33644641363     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052370h     Document Type: Article
Times cited : (59)

References (38)
  • 4
    • 2042507954 scopus 로고
    • For a review on Suzuki cross-coupling reactions, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
    • (1995) Chem. Rev. , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
  • 27
    • 33644654272 scopus 로고    scopus 로고
    • note
    • The reaction was not pushed to completion to avoid dibromo compound formation, which was previously observed. The starting methyl sulfone was recovered.
  • 30
    • 33644639699 scopus 로고    scopus 로고
    • note
    • 2O as an additive should occur and lead to a closed transition state (chairlike), as described earlier in the literature. In contrast, HMPA is known to break the complexation of the two partners, and an open transition state should operate. Nevertheless, this hypothesis cannot lead us to predict which isomer, for Z, will predominate. Further studies should be completed to validate these hypotheses.
  • 31
    • 33644662460 scopus 로고    scopus 로고
    • note
    • In Kocienski-Julia olefination, as the polarity and the coordinating ability of the solvent increase, the E selectivity of the reaction increases, which is opposite in our case with α-halomethyl sulfones, because we obtained predominantly the Z isomer. We do not have a rationale at the moment to explain this reversal.
  • 32
    • 33644658606 scopus 로고    scopus 로고
    • note
    • Julia used LDA in a mixture of THF/hexanes at -78 °C for 3 h, and then warmed the mixture to room temperature for 1 h to afford a 17:83 ratio, favoring the E alkenyl chloride.
  • 33
    • 33644653539 scopus 로고    scopus 로고
    • note
    • 2, LDA, and phosphazanes), slow addition (syringe pump over 3 h), barbier or premetalate, and different additives (monodentate, bidentate, and tridentate), without any success.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.