Modular Access to the Stereoisomers of Fused Bicyclic Azepines: Rhodium‐Catalyzed Intramolecular Stereospecific Hetero‐[5+2] Cycloaddition of Vinyl Aziridines and Alkenes |
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| Authors: | Dr Jian‐Jun Feng Tao‐Yan Lin Prof?Dr Hai‐Hong Wu Prof?Dr Junliang Zhang |
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| Institution: | Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/main.jspy |
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| Abstract: | The first rhodium‐catalyzed intramolecular hetero‐5+2] cycloaddition reaction of vinyl aziridines and alkenes was realized, wherein both internal and terminal alkenes were applicable. With this method, a variety of unique substituted chiral fused bicyclic azepines, bearing multiple contiguous stereogenic centers, were facilely accessed in a straightforward, high‐yielding, and highly stereoselective manner under mild reaction conditions. Notably, the E/Z geometry of the C?C bonds in the vinyl aziridine‐alkene substrates impact the cis/trans stereochemistry of the cycloadducts and up to six stereoisomers could be delivered. |
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| Keywords: | chirality cycloaddition heterocycles rhodium stereoselectivity |
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