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Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones
2020
Youji huaxue
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Under the catalysis of chiral amine methylated quinidine, highly diastereo-and enantioselective cyclopropanation reactions of α-bromoketones with 3-(substituted methylene) oxindoles and electron-deficient 1,3-dienes have been realized respectively, providing corresponding functionalized 3,3-spirocyclopropyl oxindoles and vinylcyclopropanes in 46%~99% yields with up to 98% ee and up to 20∶1 dr. Thus, a facile and complementary synthetic method for chiral title compounds is successfully develped by the catalytic ammonium ylide strategy.
doi:10.6023/cjoc201908034
fatcat:kq2fw4k43radfi75wsb74kiazi