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- W2801472203 endingPage "5968" @default.
- W2801472203 startingPage "5954" @default.
- W2801472203 abstract "A general protocol is described for inducing enantioselective halolactonizations of unsaturated carboxylic acids using novel bifunctional organic catalysts derived from a chiral binaphthalene scaffold. Bromo- and iodolactonization reactions of diversely substituted, unsaturated carboxylic acids proceed with high degrees of enantioselectivity, regioselectivity, and diastereoselectivity. Notably, these BINOL-derived catalysts are the first to induce the bromo- and iodolactonizations of 5-alkyl-4(Z)-olefinic acids via 5-exo mode cyclizations to give lactones in which new carbon–halogen bonds are created at a stereogenic center with high diastereo- and enantioselectivities. Iodolactonizations of 6-substituted-5(Z)-olefinic acids also occur via 6-exo cyclizations to provide δ-lactones with excellent enantioselectivities. Several notable applications of this halolactonization methodology were developed for desymmetrization, kinetic resolution, and epoxidation of Z-alkenes. The utility of these reactions is demonstrated by their application to a synthesis of precursors of the F-ring subunit of kibdelone C and to the shortest catalytic, enantioselective synthesis of (+)-disparlure reported to date." @default.
- W2801472203 created "2018-05-17" @default.
- W2801472203 creator A5042479736 @default.
- W2801472203 creator A5050500319 @default.
- W2801472203 creator A5054822594 @default.
- W2801472203 creator A5055989647 @default.
- W2801472203 creator A5064695481 @default.
- W2801472203 creator A5079343295 @default.
- W2801472203 creator A5087370616 @default.
- W2801472203 creator A5090044372 @default.
- W2801472203 date "2018-05-02" @default.
- W2801472203 modified "2023-10-14" @default.
- W2801472203 title "Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications" @default.
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