Access to spiro-bicyclo[2.1.1]hexanes via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes
Herein, we have developed a method for the construction of spiro[benzofuran-2,2′-bicyclo[2.1.1]hexanes] via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes. This transformation allowed for facile access to a variety of functionalized...
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| Veröffentlicht in: | Organic chemistry frontiers an international journal of organic chemistry 2024-01, Vol.11 (16), p.4539-4545 |
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| container_title | Organic chemistry frontiers an international journal of organic chemistry |
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| creator | Jia-Yi, Su Zhang, Jian Zhi-Yun Xin Li, Hao Zheng, Hanliang Wei-Ping, Deng |
| description | Herein, we have developed a method for the construction of spiro[benzofuran-2,2′-bicyclo[2.1.1]hexanes] via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes. This transformation allowed for facile access to a variety of functionalized spiro-bicyclo[2.1.1]hexanes in good yields (up to 99% yield) with excellent chemoselectivities and a broad substrate scope (34 examples) under mild reaction conditions. Moreover, the synthetic utility of the cycloadducts was further emphasized through a scale-up experiment and subsequent synthetic transformations. |
| doi_str_mv | 10.1039/d4qo00511b |
| format | Article |
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This transformation allowed for facile access to a variety of functionalized spiro-bicyclo[2.1.1]hexanes in good yields (up to 99% yield) with excellent chemoselectivities and a broad substrate scope (34 examples) under mild reaction conditions. 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This transformation allowed for facile access to a variety of functionalized spiro-bicyclo[2.1.1]hexanes in good yields (up to 99% yield) with excellent chemoselectivities and a broad substrate scope (34 examples) under mild reaction conditions. 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This transformation allowed for facile access to a variety of functionalized spiro-bicyclo[2.1.1]hexanes in good yields (up to 99% yield) with excellent chemoselectivities and a broad substrate scope (34 examples) under mild reaction conditions. Moreover, the synthetic utility of the cycloadducts was further emphasized through a scale-up experiment and subsequent synthetic transformations.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d4qo00511b</doi></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Benzofuran Butanes Cycloaddition Dienes Hexanes Substrates |
| title | Access to spiro-bicyclo[2.1.1]hexanes via BF3·Et2O-catalyzed formal [2π + 2σ] cycloaddition of bicyclo[1.1.0]butanes with benzofuran-derived oxa(aza)dienes |
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