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Enantioselective Friedel–Crafts Alkylation of 4,7-Dihydroindoles with Enones Catalyzed by Primary–Secondary Diamines

机译:伯-仲二胺催化的4,7-二氢吲哚对映选择性Friedel-Crafts烷基化反应

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摘要

Over the past few years, a number of chiral organocatalysts have been developed for different asymmetric transformations.[ 1] Among them, chiral secondary amines are probably the most intensively used organocatalysts. In contrast, little progress has been made in the development of chiral primary amine catalysts, probably due to unfavorable imine–secondary enamine equilibria.[2] Nevertheless, the use of chiral primary amines as organocatalysts possesses particular charm because of their known occurrence in the catalytic sites of several enzymes, such as type I aldolases, dehydratases, and decarboxylases.[3] Recently, primary amine catalysts have emerged to be effective promoters for organic processes including Michael addition, aldol, a-aminations and cycloaddition reactions.[4] Despite the recent successful applications of primary amine catalysts (mainly derived from cinchona alkaloid or 1,2-diamino-cyclohexane) in the iminium catalysis of enones, few examples have been reported for the use of primary–secondary diamine catalysts in the Michael addition reactions of enones.
机译:在过去的几年中,已经开发出许多用于不同不对称转化的手性有机催化剂。[1]其中,手性仲胺可能是使用最广泛的有机催化剂。相比之下,手性伯胺催化剂的开发进展甚微,这可能是由于亚胺-仲烯胺平衡不良所致。[2]然而,由于手性伯胺在几种酶的催化位点(例如I型醛缩酶,脱水酶和脱羧酶)的催化存在,因此手性伯胺作为有机催化剂仍然具有特殊的魅力。[3]最近,伯胺催化剂已成为有机过程的有效促进剂,包括迈克尔加成反应,醛醇缩合反应,氨基化反应和环加成反应。[4]尽管最近伯胺催化剂(主要衍生自金鸡纳生物碱或1,2-二氨基-环己烷)在烯酮的亚胺催化中成功应用,但在迈克尔加成反应中伯-仲二胺催化剂的使用报道很少。的烯酮。

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