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Synthesis 2022; 54(22): 5128-5138
DOI: 10.1055/s-0037-1610790
DOI: 10.1055/s-0037-1610790
paper
A General Way to Spiro-Annulated 2-Benzoxepines via Rh2(esp)2-Catalyzed [5+2] Cycloaddition of Diazo Arylidene Succinimides to Ketones
This research was supported by the Russian Foundation for Basic Research (project grant 21-53-12001).
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Abstract
The formation of spirocyclic 2-benzoxepines by Rh2(esp)2-catalyzed decomposition of diazo arylidene succinimides in the presence of ketones was investigated. This transformation, which is a formal [5+2] cycloaddition of styryl rhodium carbenes to the carbonyl group, occurs in high yields under mild conditions, with high carbonyl substrate tolerance and diastereoselectivity. The developed general method opens access to rare spiro (hetero)cyclic scaffolds with great potential in drug discovery.
Key words
spirocyclic scaffold - 2-benzoxepines - cyclic α-diazocarbonyl compounds - conjugated carbonyl ylide - electrocyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610790.
- Supporting Information
Publication History
Received: 11 November 2021
Accepted after revision: 08 December 2021
Article published online:
26 January 2022
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