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- W1737495447 abstract "The potential of β,γ-unsaturated α-ketothioesters participating in hetero-Diels-Alder reaction has remained unexplored. We report herein the first study of a ZnI2-catalyzed highly diastereoselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketothioesters with olefins to access highly substituted 3,4-dihydro-2H-pyrans. All the reactions proceed with cis-selectivity in moderate to excellent yields. Under similar reaction conditions, terminal alkynes undergo direct conjugate 1,4-addition to yield δ,ε-acetylenic α-ketothioesters. Furthermore, the utility of these cycloadducts has been demonstrated by an NBS-MeOH mediated stereospecific efficient access to fully substituted pyran rings. The product bromoethers undergo E2 elimination with DBU, resulting in substituted 3,6-dihydro-2H-pyrans. In addition, the thioester moiety of the products has been used for further transformations, such as amidations and Fukuyama coupling reactions." @default.
- W1737495447 created "2016-06-24" @default.
- W1737495447 creator A5021579672 @default.
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- W1737495447 creator A5070534724 @default.
- W1737495447 creator A5080505874 @default.
- W1737495447 creator A5085524872 @default.
- W1737495447 date "2015-03-09" @default.
- W1737495447 modified "2023-10-16" @default.
- W1737495447 title "ZnI<sub>2</sub>-Catalyzed Diastereoselective [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketothioesters with Olefins" @default.
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- W1737495447 doi "https://doi.org/10.1021/jo5024766" @default.
- W1737495447 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25730097" @default.
- W1737495447 hasPublicationYear "2015" @default.
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