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84859830923
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For review articles highlighting the concept of atom economy, see:
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For review articles highlighting the concept of atom economy, see:
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For early reviews, see:
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22
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84859830921
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For reviews on metal-catalyzed Meyer-Schuster rearrangements, see:
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For reviews on metal-catalyzed Meyer-Schuster rearrangements, see:
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25
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79959486571
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A protocol for the selective Meyer-Schuster rearrangement of propargylic alcohols using boronic acids as catalysts under mild conditions has been recently disclosed
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A protocol for the selective Meyer-Schuster rearrangement of propargylic alcohols using boronic acids as catalysts under mild conditions has been recently disclosed: H. Zheng, M. Lejkowski, D. G. Hall, Chem. Sci. 2011, 2, 1305-1310.
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Application of metal-catalyzed Meyer-Schuster rearrangements to the synthesis of (S)-α-ionone and prostaglandins has also been described recently:
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The mechanism of the isomerization of 2-methyl-3-butyn-2-ol into 3-methyl-2-butenal, catalyzed by an oxotitanium complex, has been previously investigated by synthesizing several compounds that model the postulated metal-oxo-propargyloxo intermediate.
-
The mechanism of the isomerization of 2-methyl-3-butyn-2-ol into 3-methyl-2-butenal, catalyzed by an oxotitanium complex, has been previously investigated by synthesizing several compounds that model the postulated metal-oxo-propargyloxo intermediate. C. Y. Lorber, M.-T. Youinou, J. Kress, J. A. Osborn, Polyhedron 2000, 19, 1693-1698.
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84859858624
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The basis of this reaction is a [3,3]-sigmatropic transposition of the metal-oxo intermediate. Similar reactions are also known for allylic alcohols using molybdenum, vanadium, or rhenium catalysts.
-
The basis of this reaction is a [3, 3]-sigmatropic transposition of the metal-oxo intermediate. Similar reactions are also known for allylic alcohols using molybdenum, vanadium, or rhenium catalysts.
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1)] is involved in the [3, 3]-sigmatropic rearrangement: see reference [16a];
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56
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48849090018
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Introduction of a Lewis acid cocatalyst able to coordinate to the C≡C bond of propargylic alcohol is also known to favor the key [3,3]-sigmatropic rearrangement step
-
Introduction of a Lewis acid cocatalyst able to coordinate to the C≡C bond of propargylic alcohol is also known to favor the key [3, 3]-sigmatropic rearrangement step: M. Egi, Y. Yamaguchi, N. Fujiwara, S. Akai, Org. Lett. 2008, 10, 1867-1870.
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see also reference [15].
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see also reference [15].
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84859871693
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2] has also been described: see reference[12].
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2] has also been described: see reference[12].
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See, for example:
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See, for example:
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75
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33846895846
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78
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84859808571
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The use of lower temperatures and/or catalyst loadings slowed down the reaction considerably; as an example, by using 1mol% of complex 2 under MW irradiation (300W) at 80°C, 3,3-diphenylpropenal was formed in only 80% GC yield after 1h.
-
The use of lower temperatures and/or catalyst loadings slowed down the reaction considerably; as an example, by using 1mol% of complex 2 under MW irradiation (300W) at 80°C, 3, 3-diphenylpropenal was formed in only 80% GC yield after 1h.
-
-
-
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79
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84859858622
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3]: see reference [21g].
-
3]: see reference [21g].
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80
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84859830924
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Such an E selectivity with secondary alkynols has been rarely observed using oxo complexes as catalysts: see reference [16a]. However, several examples of stereoselective non-oxo catalytic systems are known: see, for example, references [16b,c] and
-
Such an E selectivity with secondary alkynols has been rarely observed using oxo complexes as catalysts: see reference [16a]. However, several examples of stereoselective non-oxo catalytic systems are known: see, for example, references [16b, c] and
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84
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84859871695
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Note
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For a recent review article and a book on the chemistry of these species, see:
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85
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S. V. Druzhinin, E. S. Balenkova, V. G. Nenajdenko, Tetrahedron 2007, 63, 7753-7808;
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Nenajdenko, V.G.1
Druzhinin, S.V.2
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87
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84859808575
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3C≡CLi, generated insitu from commercially available 2-bromo-3,3,3-trifluoropropene and lithium diisopropylamide, to the corresponding carbonyl compound. See, for example:
-
3C≡CLi, generated insitu from commercially available 2-bromo-3, 3, 3-trifluoropropene and lithium diisopropylamide, to the corresponding carbonyl compound. See, for example:
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88
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0030268473
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A. R. Katritzky, M. Qi, A. P. Wells, J. Fluorine Chem. 1996, 80, 145-147;
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N. Shinohara, J. Haga, T. Yamazaki, T. Kitazume, S. Nakamura, J. Org. Chem. 1995, 60, 4363-4374;
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91
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79953846010
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3-containing secondary propargylic alcohols into enones were described recently
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3-containing secondary propargylic alcohols into enones were described recently: Y. Watanabe, T. Yamazaki, J. Org. Chem. 2011, 76, 1957-1960.
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84859808573
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Note
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3)], and AgOTf has been described to date in the literature: see reference [19b].
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95
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0037613457
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Sherry, B.D.1
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