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1
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77958072955
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Lee, J. H.; Zhang, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2010, 132, 14330-14333.
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J. Am. Chem. Soc.
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Lee, J.H.1
Zhang, Y.2
Danishefsky, S.J.3
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2
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0001272894
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De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405.
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(1991)
Org. React
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, pp. 157-405
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De Lucchi, O.1
Miotti, U.2
Modena, G.3
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4
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79851502709
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stereochemistry of this epoxide was rigorously proven by crystallographic determination of the structure of the corresponding sulfone
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The stereochemistry of this epoxide was rigorously proven by crystallographic determination of the structure of the corresponding sulfone.
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5
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34447284218
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Brajeul, S.; Delpech, B.; Marazano, C. Tetrahedron Lett. 2007, 48, 5597-5600.
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(2007)
Tetrahedron. Lett.
, vol.48
, pp. 5597-5600
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Brajeul, S.1
Delpech, B.2
Marazano, C.3
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6
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0042377537
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For a general review of activated sulfenium ions as electrophiles, see: a
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For a general review of activated sulfenium ions as electrophiles, see: (a) Nenaidenko, V. G.; Balenkova, E. S. Russ. T. Org. Chem. 2003, 39, 291-330.
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(2003)
Russ. T. Org. Chem.
, vol.39
, pp. 291-330
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Nenaidenko, V.G.1
Balenkova, E.S.2
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7
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79851495334
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For an example of a cyclization reaction that is quite different but somewhat related, see
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For an example of a cyclization reaction that is quite different but somewhat related, see:
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8
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0030925322
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(b) Nenajdenko, V. G.; Vertelezkij, P. V.; Gridnev, I. D.; Shevchenko, N. E.; Balenkova, E. S. Tetrahedron 1997, 53, 8173-8180.
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(1997)
Tetrahedron.
, vol.53
, pp. 8173-8180
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Nenajdenko, V.G.1
Vertelezkij, P.V.2
Gridnev, I.D.3
Shevchenko, N.E.4
Balenkova, E.S.5
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9
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79851481782
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8 hydroxyl. Another possibility envisions the potential of participation by the ester-like oxygen in 9 to generate a "high- energy" trifluoroacetylated oxirane, which would cleave instantaneously to provide 4. Finally, one can consider displacement of trifluoroacetate by the resident thionium species to generate the formally dipositive sulfonium, which would be hydrolytically displaced to generate the required β- hydroxysulfonium intermediate en route to the epoxide
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8 hydroxyl. Another possibility envisions the potential of participation by the ester-like oxygen in 9 to generate a "high- energy" trifluoroacetylated oxirane, which would cleave instantaneously to provide 4. Finally, one can consider displacement of trifluoroacetate by the resident thionium species to gene]rate the formally dipositive sulfonium, which would be hydrolytically displaced to generate the required β- hydroxysulfonium intermediate en route to the epoxide.
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10
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0025281231
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For a related epoxide formation from an intermediate generated in a totally different fashion, see: a, Indeed, the famous Corey methylenation of carbonyl compounds to generate oxiranes also anticipated, in its last step, a related epoxide formation. See
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For a related epoxide formation from an intermediate generated in a totally different fashion, see: (a) Corey, E. J.; Su, W. G. Tetrahedron Lett. 1990, 31, 2677-2680. Indeed, the famous Corey methylenation of carbonyl compounds to generate oxiranes also anticipated, in its last step, a related epoxide formation. See:
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(1990)
Tetrahedron. Lett.
, vol.31
, pp. 2677-2680
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Corey, E.J.1
Su, W.G.2
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12
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79851483205
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Trapping of carbon after deprotonation is a well-known cyclization method associated with the Pummerer reaction. We refer to this process as trapping a late Pummerer intermediate. The intermediates in the present work, where trapping occurs at sulfur, are described as early Pummerer intermediates
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Trapping of carbon after deprotonation is a well-known cyclization method associated with the Pummerer reaction. We refer to this process as trapping a late Pummerer intermediate. The intermediates in the present work, where trapping occurs at sulfur, are described as early Pummerer intermediates.
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14
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79851486079
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byproducts obtained in this reaction arise as a mixture of species in which the six-membered ring appears as the homoannular cyclohexadiene or one of the two isomeric conjugated methylenecyclohexenes. The formation of these products is readily accommodated in the mechanistic framework described above
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The byproducts obtained in this reaction arise as a mixture of species in which the six-membered ring appears as the homoannular cyclohexadiene or one of the two isomeric conjugated methylenecyclohexenes. The formation of these products is readily accommodated in the mechanistic framework described above.
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15
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0031435223
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For a valuable review of the traditional Pummerer reaction, see
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For a valuable review of the traditional Pummerer reaction, see: Padwa, A.; Gunn, D. E.; Osterhout, M. H. Synthesis 1997, 1353-1377.
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(1997)
Synthesis
, pp. 1353-1377
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Padwa, A.1
Gunn, D.E.2
Osterhout, M.H.3
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16
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0000813442
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Hatch, R. P.; Shringarpure, J.; Weinreb, S. M. J. Org. Chem. 1978, 43, 4172-4177.
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(1978)
J. Org. Chem.
, vol.43
, pp. 4172-4177
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Hatch, R.P.1
Shringarpure, J.2
Weinreb, S.M.3
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