Interrupted Imino‐Nazarov Cyclization of 1‐Aminopentadienyl Cation and Related Cascade Process |
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| Authors: | Ronny William Siming Wang Feiqing Ding Elise Nerissa Arviana Prof Dr Xue‐Wei Liu |
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| Affiliation: | Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore) |
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| Abstract: | Facile 4π conrotatory imino‐Nazarov cyclization of a 1‐aminopentadienyl cation generated from condensation an aldehyde and secondary aniline in the presence of a catalytic amount of a Lewis acid has been developed. Silver(I)‐catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indoline‐fused cyclopentanone. The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline‐fused cyclopentenone in a concise manner. |
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| Keywords: | cations cyclizations electrocyclization rearrangement synthetic methods |
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