ArticleAngewandte Chemie (International ed. in English)2025
Organocatalytic Enantioselective [4 + 4] Cycloadditions of Furan Ortho-Quinodimethanes.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Asymmetric Reductive Three-Component Annulation Reaction for Constructing Fused N-Heterocycles With Contiguous Stereogenic Centers.Angewandte Chemie (International ed. in English) · 2026Article
- Organocatalytic Enantioselective [4 + 4] Cycloadditions of Furan Ortho-Quinodimethanes.Angewandte Chemie (International ed. in English) · 2025Article
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7 authors.
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Abstract
The enantioselective [4 + 4] cycloaddition for the construction of cyclooctanoids is a challenging transformation in organic chemistry. Herein, we present the first organocatalytic enantioselective [4 + 4] cycloaddition of furan ortho-quinodimethanes, activated by dearomatization of the heteroaromatic compound, which thereby allows for the cycloaddition with dienes. The [4 + 4] cycloaddition is catalyzed by a quinine-derived primary amine in combination with a chiral phosphoric acid and a carboxylic acid affording cyclooctanoids isolated as a single diastereoisomer in good yields and with up to 94% ee. This reaction concept allows for the formation of cyclooctanoids without benzofusion, as demonstrated by oxidative opening of the furan ring. Computational studies of the reaction mechanism for the [4 + 4] cycloaddition point to a stepwise process. Surprisingly, the stereochemical outcome of the reaction is attributed to protonation of the two organocatalyst-bound cyclooctanoid intermediates leading to a preferred set-up for catalyst elimination to account for the absolute configuration of the cyclooctanoid.
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