ArticleChemical science2018
Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- The Catalytic Enantioselective Sommelet-Hauser Rearrangement.Journal of the American Chemical Society · 2026Article
- Understanding divergent substrate stereoselectivity in the isothiourea-catalysed conjugate addition of cyclic α-substituted β-ketoesters to α,β-unsaturated aryl esters.Chemical science · 2023Article
- Catalytic enantioselective nucleophilic desymmetrization of phosphonate esters.Nature chemistry · 2023Article
- Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2022Article
- Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.Chemical science · 2019Article
- Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes.Chemical science · 2018Article
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Authors and funding
4 authors.
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Abstract
An isothiourea-catalysed Michael addition-annulation process using β-fluoroalkyl-substituted α,β-unsaturated aryl esters and a range of 2-acylbenzazoles is reported for the enantioselective synthesis of dihydropyranone and dihydropyridinone products bearing polyfluorinated stereocenters (29 examples, up to 98% yield, >99 : 1 er). The choice of aryl group of the aryl ester proved essential in determining reaction enantioselectivity and dihydropyranone : dihydropyridinone product selectivity. The aryloxide leaving group is shown to play a number of essential additional roles, operating (i) as a Brønsted base, circumventing the need for an auxiliary base; and (ii) as a Lewis base to catalyse the isomerisation of dihydropyranone products into thermodynamically-favoured dihydropyridinones. After optimisation, this isomerisation process was exploited for the selective synthesis of dihydropyridinone products using acylbenzothiazoles, and either dihydropyranone or dihydropyridinone products using acylbenzoxazoles. Finally, the phenol derivative, produced following protonation of the aryloxide, is proposed to act as a Brønsted acid, which promotes an isothiourea-catalysed kinetic resolution of benzoxazole-derived dihydropyranones.
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