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Volumn 12, Issue 3, 2010, Pages 484-487

Regioselective synthesis of tert-allylic ethers via gold(l)-catalyzed Lntermolecular hydroalkoxylation of allenes

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EID: 75749110928     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902675k     Document Type: Article
Times cited : (64)

References (50)
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    • and references cited therein
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    • Corma, A.1    Renz, M.2
  • 13
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    • Intramolecular hydroalkoxylation of alienes, however, has been realized using a variety of different metals, including Au(I) and Au(III). For representative examples, see: (a) Winter, C.; Krause, N. Green Chem. 2009, 11, 1309.
    • (2009) Green Chem. , vol.11 , pp. 1309
    • Winter, C.1    Krause, N.2
  • 23
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    • For selected reviews on gold catalysis, see: (a) Gorin, D. J.; Toste, F. D. Nature 2007,446, 395.
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    • Gorin, D.J.1    Toste, F.D.2
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    • (BASF AG), WO-Al 9721648, 1997
    • The first report on Au(I)-catalyzed reaction of alcohols and alienes involves the sequential addition of two molecules of methanol to the central carbon of the aliene: Schulz, M.; Teles, J. H. (BASF AG), WO-Al 9721648, 1997. Chem. Abstr. 1997, 127, 121499.
    • (1997) Chem. Abstr. , vol.127 , pp. 121499
    • Schulz, M.1    Teles, J.H.2
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    • For a review on gold-catalyzed reaction of alcohols, see: Muzart, J. Tetrahedron 2008, 64, 5815.
    • (2008) Tetrahedron , vol.64 , pp. 5815
    • Muzart, J.1
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    • 50949117366 scopus 로고    scopus 로고
    • For a review on applications of NHC-Au complexes, see: Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776.
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    • Marion, N.1    Nolan, S.P.2
  • 40
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    • A control with AgOTf as the catalyst resulted in no reaction
    • A control with AgOTf as the catalyst resulted in no reaction.
  • 41
    • 75749151370 scopus 로고    scopus 로고
    • Under these optimized conditions, no isomerization of tertiary ethers 3 to primary ethers 2 is observed, regardless of the presence of excess alcohol. The excess alcohol, however, is still necessary to supress the formation of other byproducts. See Supporting Information for more details
    • Under these optimized conditions, no isomerization of tertiary ethers 3 to primary ethers 2 is observed, regardless of the presence of excess alcohol. The excess alcohol, however, is still necessary to supress the formation of other byproducts. See Supporting Information for more details.
  • 42
    • 69249248122 scopus 로고    scopus 로고
    • For a review on DMF: much more than a solvent, see: Muzart, J. Tetrahedron 2009, 65, 8313.
    • (2009) Tetrahedron , vol.65 , pp. 8313
    • Muzart, J.1
  • 50
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    • A control reaction with NIS as the reagent (without any gold catalyst) results in <5% of 29 being formed
    • A control reaction with NIS as the reagent (without any gold catalyst) results in <5% of 29 being formed.


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