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Volumn , Issue 34, 2010, Pages 6643-6650

Solvent effects on the steric course of the [2,3]-wittig rearrangement of (S,E)-[3-(Allyloxy)prop-1-ene-1,3-diyl]dibenzene and derivatives

Author keywords

Carbanions; Chirality; Configuration determination; Rearrangement; Wittig reactions

Indexed keywords


EID: 78649544309     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001061     Document Type: Article
Times cited : (13)

References (60)
  • 1
    • 18844423506 scopus 로고    scopus 로고
    • (Eds.:, Z. Rappoport, I. Marek), Wiley, Chichester
    • D. Hoppe, The Chemistry of Organolithium Compounds, vol. 1 (Eds.:, Z. Rappoport, I. Marek), Wiley, Chichester, 2004, pp. 1055-1164.
    • (2004) The Chemistry of Organolithium Compounds , vol.1 , pp. 1055-1164
    • Hoppe, D.1
  • 9
    • 78649594546 scopus 로고    scopus 로고
    • For reviews on [2,3]-Wittig rearrangements, see
    • For reviews on [2,3]-Wittig rearrangements, see
  • 27
    • 78649533031 scopus 로고    scopus 로고
    • [1h]
    • [1h]
  • 40
    • 78649616967 scopus 로고    scopus 로고
    • To secure complete deprotonation at lower temperatures, tBuLi was used
    • To secure complete deprotonation at lower temperatures, tBuLi was used.
  • 43
    • 78649607410 scopus 로고    scopus 로고
    • Use of nBuLi as a base resulted in the formation of a butyl ketone derivative as a byproduct in the case of (S)- 6e and (S)- 6f
    • Use of nBuLi as a base resulted in the formation of a butyl ketone derivative as a byproduct in the case of (S)- 6e and (S)- 6f.
  • 44
    • 78649585065 scopus 로고    scopus 로고
    • [20a]
    • [20a]
  • 46
    • 78649540700 scopus 로고    scopus 로고
    • The m.p. of 1,4-dioxane is 11 °C
    • The m.p. of 1,4-dioxane is 11 °C.
  • 47
    • 78649578295 scopus 로고    scopus 로고
    • Although the origin of the different temperature dependencies of the rates for the organolithium racemization and the reaction with aldehyde is not clear, the same trend is observed in the [2,3]-Wittig rearrangement (Table 3)
    • Although the origin of the different temperature dependencies of the rates for the organolithium racemization and the reaction with aldehyde is not clear, the same trend is observed in the [2,3]-Wittig rearrangement (Table 3).
  • 48
    • 78649571278 scopus 로고    scopus 로고
    • We reported that [2,3]-Wittig rearrangement of the type observed with 4 proceeds with inversion of configuration at the lithium-bearing carbon atom in the same way as reported for the alkyl counterparts, see
    • We reported that [2,3]-Wittig rearrangement of the type observed with 4 proceeds with inversion of configuration at the lithium-bearing carbon atom in the same way as reported for the alkyl counterparts, see
  • 53
    • 78649589250 scopus 로고    scopus 로고
    • Although the hypothesis is not in accord with the widely accepted mechanism for [2,3]-Wittig rearrangement, there is no report in the literature to the best of our knowledge on the enantioselective [2,3]-Wittig rearrangement by using relatively stable chiral carbanions such as that generated from 4 in nonpolar solvents
    • Although the hypothesis is not in accord with the widely accepted mechanism for [2,3]-Wittig rearrangement, there is no report in the literature to the best of our knowledge on the enantioselective [2,3]-Wittig rearrangement by using relatively stable chiral carbanions such as that generated from 4 in nonpolar solvents.
  • 55
    • 77249160190 scopus 로고    scopus 로고
    • and references cited therein
    • N. Deora, P. R. Carlier, J. Org. Chem. 2010, 75, 1061-1069 and references cited therein.
    • (2010) J. Org. Chem. , vol.75 , pp. 1061-1069
    • Deora, N.1    Carlier, P.R.2
  • 56
    • 51749083024 scopus 로고    scopus 로고
    • and references cited therein
    • H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911 and references cited therein.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 11901-11911
    • Ott, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.