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Synthesis 2022; 54(22): 5128-5138
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

Anastasia Vepreva
a   Saint Petersburg State University, Petersburg, 199034, Russian Federation
,
Grigory Kantin
a   Saint Petersburg State University, Petersburg, 199034, Russian Federation
,
Mikhail Krasavin  ∗
a   Saint Petersburg State University, Petersburg, 199034, Russian Federation
b   Immanuel Kant Baltic Federal University, Kaliningrad 236041, Russian Federation
,
Dmitry Dar’in  ∗
a   Saint Petersburg State University, Petersburg, 199034, Russian Federation
› InstitutsangabenThis 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 - electrocyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610790.
  • Supporting Information


Publikationsverlauf

Eingereicht: 11. November 2021

Angenommen nach Revision: 08. Dezember 2021

Artikel online veröffentlicht:
26. Januar 2022

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