Stereoselective Synthesis of Polycycles Containing an Aziridine Group: Intramolecular aza‐Diels–Alder Reactions of Unactivated 2H‐Azirines with Unactivated Dienes |
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Authors: | Dr Hua‐Dong Xu Hao Zhou Ying‐Peng Pan Xin‐Tao Ren Hao Wu Mei Han Run‐Ze Han Dr Mei‐Hua Shen |
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Institution: | School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou, Jiangsu Province, China |
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Abstract: | Vinyl azide with a pendent diene can undergo thermal decomposition to a related azirine intermediate, which was used immediately in an intramolecular aza‐Diels–Alder reaction to furnish an aziridine‐containing trans‐fused tricyclic core structure with excellent stereoselectivity. The method provides a facile entry to complex polycyclic alkaliods which can be further elaborated by ring‐opening reactions and ring expansion of the aziridine moiety, as well as by dihydroxylation of the alkene group. |
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Keywords: | aziridines cycloadditions heterocycles small-ring systems synthetic methods |
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