ArticleThe Journal of organic chemistry2025
Enantioselective Synthesis of Spirocyclic Isoxazolones Using a Conia-Ene Type Reaction.
Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Synthesis of Trifluoromethylated Spiroisoxazolones via a [3+2] Cycloaddition of Nitrile Imines and Unsaturated Isoxazolones.Molecules (Basel, Switzerland) · 2025Article
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4 authors.
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Abstract
Stereoselective synthesis of spirocyclic compounds containing heterocyclic motifs represents a formidable challenge in enantioselective synthesis. Here, we present a cascade reaction between α,β-unsaturated aldehydes and isoxazolones under synergistic catalysis of a chiral secondary amine and a palladium(0) catalyst. This strategy allows access to chiral spiroisoxazolone derivatives with a large substrate scope tolerance and high levels of diastereoselectivity (dr up to 20:1) and enantioselectivity (up to 99% ee). Furthermore, the utility of this methodology is showcased by the transformation of chiral spiroisoxazolones into structurally attractive and enantiomerically enriched cyclopentene carboxylic acids with two stereogenic centers.
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