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Facile 4pi 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. Taking control: The fate of an oxyallyl cation formed through a 4pi conrotatory imino-Nazarov cyclization can be controlled to access cyclopentanoid frameworks. In the presence of silver(I), intramolecular arene trapping leads to indoline-fused cyclopentanones. Gadolinium(III) facilitates a cascade transformation to furnish tetrahydroquinoline-fused cyclopentenones. Tf=trifluoromethanesulfonyl.
Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 22013-33-8Related Products of 22013-33-8.