title: Regiodivergent Intermolecular [3+2] Cycloadditions of Vinyl Aziridines and Allenes: Stereospecific Synthesis of Chiral Pyrrolidines.
abstract: The first rhodium-catalyzed intermolecular [3+2] cycloaddition reaction of vinyl aziridines and allenes for the synthesis of enantioenriched functionalized pyrrolidines was realized. [3+2] cycloaddition with the proximal C=C bond of N-allenamides gave 3-methylene-pyrrolidines in high regio- and diastereoselectivity, whereas, 2-methylene-pyrrolidines were obtained as the major products by the cycloadditions of vinyl aziridines with the distal C=C bond of allenes. Use of readily available starting materials, a broad substrate scope, high selectivity, mild reaction conditions, as well as versatile functionalization of the cycloadducts make this approach very practical and attractive.
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.
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.
authors.forename: Chao-Ze
authors.initials: CZ
authors.lastname: Zhu
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.
authors.forename: Peichao
authors.initials: P
authors.lastname: Zhang
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.
authors.forename: Yidong
authors.initials: Y
authors.lastname: Wang
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.
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. jjfeng@chem.ecnu.edu.cn.
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. jlzhang@chem.ecnu.edu.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai, 200032, China. jlzhang@chem.ecnu.edu.cn.
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhang
keywords: allenes; chirality; cycloaddition; heterocycles; rhodium