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- W2256094689 abstract "We report a synthetic strategy for a chemoselective switch and a diastereo-divergent approach for the asymmetric reaction of 5H-oxazol-4-ones and N-itaconimides catalyzed by l-tert-leucine-derived tertiary amine-urea compounds. The reaction was modulated to harness either tandem conjugate addition-protonation or [4+2] cycloaddition as major product with excellent enantio- and diastereoselectivities. Subjecting the enantio-enriched cycloaddition products to a basic silica gel reagent yields the diastereomer vis-à-vis the product directly obtained under conditions for addition-protonation, thus opening a diastereo-divergent route for creating 1,3-tertiary-hetero-quaternary stereocenters. Quantum chemical studies further provide stereochemical analysis for the [4+2] process and a plausible mechanism for this chemoselective switch is proposed." @default.
- W2256094689 created "2016-06-24" @default.
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- W2256094689 date "2015-12-09" @default.
- W2256094689 modified "2023-10-09" @default.
- W2256094689 title "Chemoselective Switch in the Asymmetric Organocatalysis of 5<i>H</i>-Oxazol-4-ones and<i>N</i>-Itaconimides: Addition-Protonation or [4+2] Cycloaddition" @default.
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- W2256094689 doi "https://doi.org/10.1002/anie.201507796" @default.
- W2256094689 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/26662073" @default.
- W2256094689 hasPublicationYear "2015" @default.
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