摘要/Abstract

在甲基化奎尼丁（20 mol%）的催化下，分别实现了α-溴代酮与3-（取代亚甲基）吲哚酮和缺电子1，3-二烯的高度非对映选择性和对映选择性的环丙烷化反应，以46%~99%收率、高达98%ee和20：1 dr生成相应的3，3-螺环丙基吲哚酮和乙烯基环丙烷.通过催化的氮叶立德策略，成功发展了一种用于上述手性化合物的简便合成方法.
关键词: 手性胺, [2+1]环化反应, α-溴代酮, 不对称合成
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.
Key words: chiral amine, [2+1] annulation reaction, α-bromoketone, asymmetric synthesis


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