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Volumn 10, Issue 8, 2008, Pages 1569-1572

Gold(I)-catalyzed rearrangement of alkynloxiranes: A mild access to divinyl ketones

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EID: 52049117956     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800219k     Document Type: Article
Times cited : (66)

References (50)
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    • For recent reviews on gold chemistry, see
    • For recent reviews on gold chemistry, see:
  • 2
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    • (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
    • (2007) Chem. Rev , vol.107 , pp. 3180-3211
    • Hashmi, A.S.K.1
  • 18
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    • Gold(I)-catalyzed cascade reactions involving cyclization of δ-alkynyl epoxides and further water or alcohol addition were also recently described. See: Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191-3194.
    • Gold(I)-catalyzed cascade reactions involving cyclization of δ-alkynyl epoxides and further water or alcohol addition were also recently described. See: Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191-3194.
  • 19
    • 58149182118 scopus 로고    scopus 로고
    • Hashmi has nevertheless shown that the presence of primary alcohol on the substrate did not affect the formation of furans (Scheme 1, R1, CH2)4OH).5 Therefore, in this case, the nucleophilic alcohol seems to be too far to interact with the alkynyloxirane part
    • 5 Therefore, in this case, the nucleophilic alcohol seems to be too far to interact with the alkynyloxirane part.
  • 26
    • 58149198353 scopus 로고    scopus 로고
    • 2/Pd(II) via allene intermediates:
    • 2/Pd(II) via allene intermediates:
  • 30
    • 58149192596 scopus 로고    scopus 로고
    • Ag salts are known to promote rearrangement of propargyl acetoxy derivatives
    • Ag salts are known to promote rearrangement of propargyl acetoxy derivatives:
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    • (a) Benn, W. R. J. Org. Chem. 1968, 33, 3113-3118.
    • (1968) J. Org. Chem , vol.33 , pp. 3113-3118
    • Benn, W.R.1
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    • 1H NMR did not show the presence of intermediates of the Z isomer 2j. However, the faster conversion of one of the two isomers of lj was observed.
    • 1H NMR did not show the presence of intermediates of the Z isomer 2j. However, the faster conversion of one of the two isomers of lj was observed.
  • 38
    • 58149192281 scopus 로고    scopus 로고
    • 11) furnished poor yield of divinyl ketone (10 %) but again no trace of furane was observed even after a long contact time.
    • 11) furnished poor yield of divinyl ketone (10 %) but again no trace of furane was observed even after a long contact time.
  • 42
    • 58149192589 scopus 로고    scopus 로고
    • 2O gave lk in good yield. See the Supporting Information.
    • 2O gave lk in good yield. See the Supporting Information.
  • 48
    • 58149184466 scopus 로고    scopus 로고
    • Such type of substrates can potentially lead to the formation of the corresponding useful cyclopentenones via the Nazarov reaction. For reviews, see
    • Such type of substrates can potentially lead to the formation of the corresponding useful cyclopentenones via the Nazarov reaction. For reviews, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.