title: Modular Access to the Stereoisomers of Fused Bicyclic Azepines: Rhodium-Catalyzed Intramolecular Stereospecific Hetero-[5+2] Cycloaddition of Vinyl Aziridines and Alkenes.
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.
authors.affiliation: 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.
authors.forename: Jian-Jun
authors.initials: JJ
authors.lastname: Feng
authors.affiliation: 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.
authors.forename: Tao-Yan
authors.initials: TY
authors.lastname: Lin
authors.affiliation: 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.
authors.forename: Hai-Hong
authors.initials: HH
authors.lastname: Wu
authors.affiliation: 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. jlzhang@chem.ecnu.edu.cn.
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhang
keywords: chirality; cycloaddition; heterocycles; rhodium; stereoselectivity