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Volumn 50, Issue 7, 2011, Pages 1664-1667

Enantioselective construction of bridged multicyclic skeletons: Intermolecular [2+2+2] cycloaddition/intramolecular diels-alder reaction cascade

Author keywords

asymmetric catalysis; cascade reactions; cycloaddition; Diels Alder reaction; rhodium

Indexed keywords

ASYMMETRIC CATALYSIS; CASCADE REACTIONS; DIELS-ALDER REACTION; ENANTIOSELECTIVE CONSTRUCTION; LIGAND COMPLEXES;

EID: 79851481023     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004150     Document Type: Article
Times cited : (46)

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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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    • 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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    • 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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