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For examples, see
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79851483877
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Recently, chiral hypervalent iodine catalyzed enantioselective oxidative spirolactonizations of 1-naphthol derivatives were reported. See
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For reviews of transition-metal-catalyzed enantioselective [2+2+2] cycloadditions, see
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For our account, see
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For our account, see:, K. Tanaka, Synlett 2007, 1977.
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K. Tsuchikama, Y. Kuwata, T. Shibata, J. Am. Chem. Soc. 2006, 128, 13686. For rhodium-catalyzed enantioselective [2+2+2] cycloadditions of 1,6-diynes with enamides and an acrylamide, see
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79851476532
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For iridium-catalyzed [2+2+2] cycloadditions of a 1,6-diyne with enol ethers, see
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For iridium-catalyzed [2+2+2] cycloadditions of a 1,6-diyne with enol ethers, see
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30
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30744465624
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For rhodium-catalyzed [2+2+2] cycloadditions of alkynes with enol ethers and acetates, see
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S. Kezuka, S. Tanaka, T. Ohe, Y. Nakaya, R. Takeuchi, J. Org. Chem. 2006, 71, 543. For rhodium-catalyzed [2+2+2] cycloadditions of alkynes with enol ethers and acetates, see
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For rhodium-catalyzed [2+2+2] cycloadditions of 1,6- and 1,7-diynes with vinylene carbonate, see
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H. Hara, M. Hirano, K. Tanaka, Tetrahedron 2009, 65, 5093. For rhodium-catalyzed [2+2+2] cycloadditions of 1,6- and 1,7-diynes with vinylene carbonate, see
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A ruthenium(II)-catalyzed, one-pot [2+2+2]/[4+2] cycloaddition of one terminal 1,6-diyne with two N-phenylmaleimides was reported. See
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A ruthenium(II)-catalyzed, one-pot [2+2+2]/[4+2] cycloaddition of one terminal 1,6-diyne with two N-phenylmaleimides was reported. See:, Y. Yamamoto, H. Kitahara, R. Ogawa, H. Kawaguchi, K. Tatsumi, K. Itoh, J. Am. Chem. Soc. 2000, 122, 4310.
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72449133952
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The reaction of 1,6-diyne 1a and sterically more demanding styryl methacrylate was also investigated. However, the [2+2+2] cycloaddition of the enol double bond, and not the methacrylic double bond, occurred and this was followed by aromatization to yield the corresponding substituted benzene. As well as this product, the carboxylative cyclization product of 1a with methacrylic acid and the homo-[2+2+2] cycloaddition product of 1a were generated. For the rhodium-catalyzed carboxylative cyclization of 1,6-diynes, see
-
The reaction of 1,6-diyne 1a and sterically more demanding styryl methacrylate was also investigated. However, the [2+2+2] cycloaddition of the enol double bond, and not the methacrylic double bond, occurred and this was followed by aromatization to yield the corresponding substituted benzene. As well as this product, the carboxylative cyclization product of 1a with methacrylic acid and the homo-[2+2+2] cycloaddition product of 1a were generated. For the rhodium-catalyzed carboxylative cyclization of 1,6-diynes, see:, K. Tanaka, S. Saito, H. Hara, Y. Shibata, Org. Biomol. Chem. 2009, 7, 4817.
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For a review of chemo- and regioselective intermolecular [2+2+2] cycloadditions, see
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For a review of chemo- and regioselective intermolecular [2+2+2] cycloadditions, see:, B. R. Galan, T. Rovis, Angew. Chem. 2009, 121, 2870
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For transition-metal-catalyzed enantioselective intermolecular [2+2+2] cycloadditions of two identical alkynes with one alkene, see
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For transition-metal-catalyzed enantioselective intermolecular [2+2+2] cycloadditions of two identical alkynes with one alkene, see
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79851472732
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For transition-metal-catalyzed intermolecular [2+2+2] cycloadditions of two different alkynes and one alkene, see
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Refs. [8b] and [8c]. For related transition-metal-catalyzed [3+2+2] cycloadditions, see
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Refs. [8b] and [8c]. For related transition-metal-catalyzed [3+2+2] cycloadditions, see
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46
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79851475296
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CCDCa 782581 [(-)- 3aa ], CCDCa 782582 [(+)- 3ae ], CCDCa 782583 [(+)- 3gc ], and CCDCa 782584 [(+)- 7ada ] contain the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
CCDCa 782581 [(-)- 3aa ], CCDCa 782582 [(+)- 3ae ], CCDCa 782583 [(+)- 3gc ], and CCDCa 782584 [(+)- 7ada ] contain the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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50
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79851494957
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A control experiment was conducted to see if the rhodium catalyst is required for the Diels-Alder reaction step. As a result of this control experiment, it was concluded that the rhodium catalyst is not necessary for the Diels-Alder reaction step. See the Supporting Information
-
A control experiment was conducted to see if the rhodium catalyst is required for the Diels-Alder reaction step. As a result of this control experiment, it was concluded that the rhodium catalyst is not necessary for the Diels-Alder reaction step. See the Supporting Information.
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