Regiodivergent Intermolecular [3+2] Cycloadditions of Vinyl Aziridines and Allenes: Stereospecific Synthesis of Chiral Pyrrolidines |
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| Authors: | Tao‐Yan Lin Chao‐Ze Zhu Peichao Zhang Yidong Wang Prof. Dr. Hai‐Hong Wu Dr. Jian‐Jun Feng Prof. Dr. Junliang Zhang |
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| Affiliation: | 1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, P.R. China;2. http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, China |
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| 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. |
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| Keywords: | cycloaddition allenes chirality heterocycles rhodium |
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