Concise [4+3] cycloaddition reaction of pyrroles leading to tropinone derivatives |
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| Authors: | Ryuichi FuchigamiKosuke Namba Keiji Tanino |
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| Institution: | a Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-0810, Japan
b Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan |
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| Abstract: | A concise 4+3] cycloaddition reaction of pyrroles with 2-(silyloxy)allyl cations has been developed. The oxyallyl cations stabilized with a methylthio group or geminal methyl groups were generated from the corresponding allylic alcohols under the influence of a Brönsted acid (Tf2NH), respectively. The use of N-nosyl-protected pyrroles as the four-carbon unit was found to give tropinone derivatives in high yield. |
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| Keywords: | Tropinone [4+3] Cycloaddition reaction Pyrroles Oxyallyl cation Sulfur-stabilized cation |
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