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1
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70349945822
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For recent reviews on the Bergman, Saito-Myers, and Moore cyclizations, see
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For recent reviews on the Bergman, Saito-Myers, and Moore cyclizations, see
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For recent reviews, see
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33344468391
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I-catalyzed tandem [3, 3]-sigmatropic rearrangement /formal Saito-Myers cyclization of propargyl esters to form aromatic ketones, see
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I-catalyzed tandem [3, 3]-sigmatropic rearrangement /formal Saito-Myers cyclization of propargyl esters to form aromatic ketones, see
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28
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70349955169
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Compound 4a is, in fact, a 5-substituted salicylic ester; this subunit, which is quite difficult to prepare because of steric hindrance, is present in several natural products and synthethic compounds with relevant biological activity:
-
Compound 4a is, in fact, a 5-substituted salicylic ester; this subunit, which is quite difficult to prepare because of steric hindrance, is present in several natural products and synthethic compounds with relevant biological activity:
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30
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17044384198
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Angew. Chem. Int. Ed. 2005, 44, 1696-1699;
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32
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70349961929
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In particular, (2E, 4Z) -6-methoxycarbonyl-5-phenyl-2, 4-hexadienoic acid (5), which results from the formal hydration of 2a, was isolated (81%) when the reaction was performed in MeOH.
-
In particular, (2E, 4Z) -6-methoxycarbonyl-5-phenyl-2, 4-hexadienoic acid (5), which results from the formal hydration of 2a, was isolated (81%) when the reaction was performed in MeOH.
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33
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70349936633
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See the Supporting Information
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See the Supporting Information.
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-
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34
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70349949305
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The effects of ligands in homogeneous gold catalysis has been recently revised, see
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The effects of ligands in homogeneous gold catalysis has been recently revised, see
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35
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51049105959
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D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378;
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Gorin, D.J.1
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37
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67749091068
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The gold-catalyzed hydration of a triple bond has been recently reported with as low as 10 ppm catalyst loading: N Marion, R. S. Ramon, S. P. Nolan, J. Am. Chem. Soc. 2009, 131, 448-449.
-
The gold-catalyzed hydration of a triple bond has been recently reported with as low as 10 ppm catalyst loading: N Marion, R. S. Ramon, S. P. Nolan, J. Am. Chem. Soc. 2009, 131, 448-449.
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-
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38
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37249012791
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For example, the gold-catalyzed intramolecular carbocyclization of alkynyl ketones requires heating at 100°8C with a 2-5 mol% catalyst loading: T Jin, Y Yamamoto, Org. Lett. 2007, 9, 5259-5262;
-
a) For example, the gold-catalyzed intramolecular carbocyclization of alkynyl ketones requires heating at 100°8C with a 2-5 mol% catalyst loading: T Jin, Y Yamamoto, Org. Lett. 2007, 9, 5259-5262;
-
-
-
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39
-
-
56949099150
-
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when 1,3-enynyl carbonyl compounds are employed, a gold-catalyzed tandem heteroenyne metathesis and Nazarov reaction takes place at 50-1008°C: T Jin, Y. Yamamoto, Org. Lett. 2008, 10, 3137-3139.
-
when 1,3-enynyl carbonyl compounds are employed, a gold-catalyzed tandem heteroenyne metathesis and Nazarov reaction takes place at 50-1008°C: T Jin, Y. Yamamoto, Org. Lett. 2008, 10, 3137-3139.
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-
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40
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33644949668
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The regioselectivity depends on the substitution pattern of the triple bond for the intramolecular gold-catalyzed cycloisomerization of acetylenic carboxylic acids: E. Genin, P. Y. Toullec, S. Antoniotti, C Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112-3113
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The regioselectivity depends on the substitution pattern of the triple bond for the intramolecular gold-catalyzed cycloisomerization of acetylenic carboxylic acids: E. Genin, P. Y. Toullec, S. Antoniotti, C Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112-3113.
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-
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41
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70349955172
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For an interesting discussion regarding the nature of intermediates in gold-catalyzed reactions, see
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For an interesting discussion regarding the nature of intermediates in gold-catalyzed reactions, see
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43
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53249152128
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Angew. Chem. Int. Ed. 2008, 47, 6754-6756;
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45
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53049098944
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for a mechanistic perspective review on gold-catalyzed cycloisomerizations of enynes, see
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Angew. Chem. Int. Ed. 2008, 47, 5030-5033; for a mechanistic perspective review on gold-catalyzed cycloisomerizations of enynes, see
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(2008)
Angew. Chem. Int. Ed
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-
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47
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70349963203
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Alternatively, a 6π electrocyclization through mesomeric intermediate IIIb may take place to give IV.
-
Alternatively, a 6π electrocyclization through mesomeric intermediate IIIb may take place to give IV.
-
-
-
-
48
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70349950870
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-
13C shifts of the |3-alkyne carbon atom in the NMR spectra of compounds 2 (δ = 33.9-39.5 ppm) versus 6a-d (δ = 84.3-87.3 ppm) and 6e (δ = 85.8 ppm).
-
13C shifts of the |3-alkyne carbon atom in the NMR spectra of compounds 2 (δ = 33.9-39.5 ppm) versus 6a-d (δ = 84.3-87.3 ppm) and 6e (δ = 85.8 ppm).
-
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49
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34848858217
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(M.) Hii
-
and references therein. For general methodologies for the synthesis of unsymmetrical terphenyls, see
-
For general methodologies for the synthesis of unsymmetrical terphenyls, see J. M. Antelo Míguez, L. A. Adrio, A. Sousa-Pedrares, J. M. Vila, K. K. (M.) Hii, J. Org. Chem. 2007, 72, 7771-7774, and references therein.
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Vila, K.K.5
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