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Catalyst-controlled formal [4 + 1] annulation of N-vinyl fluorenone nitrones and allenoates to prepare spirofluorenylpyrrolines

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Abstract

We report a facile commercial gimeracil-catalyzed formal [4 + 1] annulation approach for the synthesis of spirofluorenylpyrrolines in good yields with high diastereoselectivity from easily available N-vinyl fluorenone nitrones and allenoates. The reaction showed broad substrate scope and tolerated a variety of functional groups on both N-vinyl fluorenone nitrones and allenoates. Mechanistic studies showed that the catalyst might play important roles in promoting enolation and selective cyclization of 1,3-dicarbonyl intermediates. More importantly, the obtained spirofluorenylpyrrolines were easily converted to various spirofluorenylpyrroline-based scaffolds.

Graphical abstract: Catalyst-controlled formal [4 + 1] annulation of N-vinyl fluorenone nitrones and allenoates to prepare spirofluorenylpyrrolines

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Article information


Submitted
16 Feb 2020
Accepted
02 May 2020
First published
08 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Catalyst-controlled formal [4 + 1] annulation of N-vinyl fluorenone nitrones and allenoates to prepare spirofluorenylpyrrolines

C. Wei, J. Zhang, J. Zhang, C. Liang and D. Mo, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00224K

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