PtCl4-Catalyzed Domino Synthesis of Fused Bicyclic Acetals
At sixes and sevens: The synthesis of [4.2.1]‐ and [3.2.1]‐fused bicyclic acetals by an intramolecular double alkoxylation of alkyne diols is reported. The course of the reaction depends on the substitution of the triple bond. Terminal alkynes give the [3.2.1]bicyclic product by a 6‐exo pathway, whe...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2008-01, Vol.47 (1), p.209-212 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Diéguez-Vázquez, Alejandro Tzschucke, C. Christoph Lam, Wing Yee Ley, Steven V. |
| description | At sixes and sevens: The synthesis of [4.2.1]‐ and [3.2.1]‐fused bicyclic acetals by an intramolecular double alkoxylation of alkyne diols is reported. The course of the reaction depends on the substitution of the triple bond. Terminal alkynes give the [3.2.1]bicyclic product by a 6‐exo pathway, whereas aryl alkynes undergo almost exclusively a 7‐endo cyclization to give the [4.2.1]bicycles (see scheme, Ts=toluene‐4‐sulfonyl). |
| doi_str_mv | 10.1002/anie.200704595 |
| format | Article |
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Terminal alkynes give the [3.2.1]bicyclic product by a 6‐exo pathway, whereas aryl alkynes undergo almost exclusively a 7‐endo cyclization to give the [4.2.1]bicycles (see scheme, Ts=toluene‐4‐sulfonyl).</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200704595</identifier><identifier>PMID: 18061909</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Acetals - chemical synthesis ; Acetals - chemistry ; Bridged Bicyclo Compounds - chemical synthesis ; Bridged Bicyclo Compounds - chemistry ; Catalysis ; Cyclization ; domino reactions ; fused-ring systems ; hydroalkoxylation ; Molecular Conformation ; platinum ; Platinum Compounds - chemistry ; Stereoisomerism</subject><ispartof>Angewandte Chemie International Edition, 2008-01, Vol.47 (1), p.209-212</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. 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Terminal alkynes give the [3.2.1]bicyclic product by a 6‐exo pathway, whereas aryl alkynes undergo almost exclusively a 7‐endo cyclization to give the [4.2.1]bicycles (see scheme, Ts=toluene‐4‐sulfonyl).</description><subject>Acetals - chemical synthesis</subject><subject>Acetals - chemistry</subject><subject>Bridged Bicyclo Compounds - chemical synthesis</subject><subject>Bridged Bicyclo Compounds - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>domino reactions</subject><subject>fused-ring systems</subject><subject>hydroalkoxylation</subject><subject>Molecular Conformation</subject><subject>platinum</subject><subject>Platinum Compounds - chemistry</subject><subject>Stereoisomerism</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkEtPwzAQhC0EoqVw5Yhy4pZix3EccyuhbYpQQTyKxMVybEcY0qTEiSD8ely1lNPsar9ZaQaAUwSHCMLgQpRGDwMIKQwJI3ugj0iAfEwp3ndziLFPY4J64Mjad8fHMYwOQQ85QQyyPri8b5Ii9BPRiKL70cq7rpamrLzHrmzetDXWq3Jv0lp3uTKyk4WR3khqR9tjcJA70SdbHYDnyfgpSf3bu-ksGd36BkeY-HGOCNFZEEZZHFCilYyZEjSmEEU0V0rmNGQ6RpFWIQtUiHNIhMwwQ0Llkkg8AOebv6u6-my1bfjSWKmLQpS6ai13j1xmxBx4tgXbbKkVX9VmKeqO_6V1ANsAX6bQ3f8d8nWXfN0l33XJR_PZeLc5r7_xGtvo751X1B88opgS_jKf8vT1ZrFIFw88xb_g3XZX</recordid><startdate>20080101</startdate><enddate>20080101</enddate><creator>Diéguez-Vázquez, Alejandro</creator><creator>Tzschucke, C. 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Terminal alkynes give the [3.2.1]bicyclic product by a 6‐exo pathway, whereas aryl alkynes undergo almost exclusively a 7‐endo cyclization to give the [4.2.1]bicycles (see scheme, Ts=toluene‐4‐sulfonyl).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>18061909</pmid><doi>10.1002/anie.200704595</doi><tpages>4</tpages></addata></record> |
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| subjects | Acetals - chemical synthesis Acetals - chemistry Bridged Bicyclo Compounds - chemical synthesis Bridged Bicyclo Compounds - chemistry Catalysis Cyclization domino reactions fused-ring systems hydroalkoxylation Molecular Conformation platinum Platinum Compounds - chemistry Stereoisomerism |
| title | PtCl4-Catalyzed Domino Synthesis of Fused Bicyclic Acetals |
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