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Volumn 47, Issue 43, 2006, Pages 7533-7535

A facile and stereoselective synthetic method for allylic 1,3-dienyl ethers

Author keywords

1,4 Elimination; Allylic 1,3 dienyl ethers; Claisen rearrangement; Cope rearrangement; Wittig rearrangement

Indexed keywords

ETHER DERIVATIVE;

EID: 33748747033     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.100     Document Type: Article
Times cited : (10)

References (32)
  • 1
    • 0000746177 scopus 로고
    • Trost B.M. (Ed), Pergamon, Oxford Chapter 7.2
    • Wipf P. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford Chapter 7.2
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Wipf, P.1
  • 7
    • 33644652968 scopus 로고    scopus 로고
    • Previously, the 1,4-elimination reactions have reported using α,β-unsaturated acetals:
    • Previously, the 1,4-elimination reactions have reported using α,β-unsaturated acetals:. Pichon N., Harrison-Marchand A., Toupet L., and Maddaluno J. J. Org. Chem. 71 (2006) 1892
    • (2006) J. Org. Chem. , vol.71 , pp. 1892
    • Pichon, N.1    Harrison-Marchand, A.2    Toupet, L.3    Maddaluno, J.4
  • 19
    • 0000952950 scopus 로고
    • A example of 1,4-elimination reaction of 1,4-dialkoxy-(2Z)-butene:
    • A example of 1,4-elimination reaction of 1,4-dialkoxy-(2Z)-butene:. Margot C., Matsuda H., and Schlosser M. Tetrahedron 46 (1990) 2425
    • (1990) Tetrahedron , vol.46 , pp. 2425
    • Margot, C.1    Matsuda, H.2    Schlosser, M.3
  • 20
    • 33645791244 scopus 로고    scopus 로고
    • For reviews:. Rappoport Z., and Marek I. (Eds), John Wiley & Sons Ltd., Chichester
    • For reviews:. Tomooka K. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 2 (2004), John Wiley & Sons Ltd., Chichester 749-828
    • (2004) The Chemistry of Organolithium Compounds , vol.2 , pp. 749-828
    • Tomooka, K.1
  • 21
    • 33748742848 scopus 로고    scopus 로고
    • Baldwin J.E., and Williams R.M. (Eds), Pergamon, Manchester Chapter 8
    • Clayden J. In: Baldwin J.E., and Williams R.M. (Eds). Organolithiums: Selectivity for Synthesis (2002), Pergamon, Manchester Chapter 8
    • (2002) Organolithiums: Selectivity for Synthesis
    • Clayden, J.1
  • 24
    • 0000002499 scopus 로고
    • Trost B.M. (Ed), Pergamon, Oxford Chapter 4.6
    • Brückner R. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 6 (1991), Pergamon, Oxford Chapter 4.6
    • (1991) Comprehensive Organic Synthesis , vol.6
    • Brückner, R.1
  • 25
    • 33748740783 scopus 로고    scopus 로고
    • note
    • 4NBr, allyl bromide, benzene, 50% aq NaOH, rt. Details: see Supplementary data.
  • 26
    • 33748748088 scopus 로고    scopus 로고
    • note
    • Use of sec- or tert-butyllithium instead of n-butyllithium resulted in lower yields due to de-allylation of 1a.
  • 27
    • 33748745156 scopus 로고    scopus 로고
    • note
    • A similar reaction of 1-allyloxy-4-methoxy-(2E)-undecene [(E)-1a] in ether was found to give a geometric mixture of 2a in a 31% yield [(1Z,3E)/(1Z,3Z) = 6:4] and a complicated diastereomixture of 3a in a 10% yield with the recovery of the starting material in 37% yield.
  • 28
    • 33748743760 scopus 로고    scopus 로고
    • note
    • 2O instead of THF gave almost the same result.
  • 30
    • 33748741588 scopus 로고    scopus 로고
    • note
    • 2 (1 atm), Lindlar-cat., quinoline, EtOAc, rt. Details: see Supplementary data.
  • 31
    • 33748755913 scopus 로고    scopus 로고
    • note
    • Examples of 1,4-elimination reaction of γ-benzylicoxy-α,β-unsaturated acetals have been reported: see Ref. 3b and c.
  • 32
    • 0000002499 scopus 로고
    • Trost B.M. (Ed), Pergamon, Oxford Chapter 7.3
    • Ziegler F.E. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford Chapter 7.3
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Ziegler, F.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.