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首页> 外文期刊>Chemistry: A European journal >Regioselective synthesis of β-aryl- and β-amino-substituted aliphatic esters by rhodium-catalyzed tandem double-bond migration/conjugate addition
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Regioselective synthesis of β-aryl- and β-amino-substituted aliphatic esters by rhodium-catalyzed tandem double-bond migration/conjugate addition

机译：通过Rhodium催化串联双键迁移/缀合物添加β-芳基和β-氨基取代的脂族酯的区域选择性合成

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摘要

Rhodium-phosphite catalysts were found to effectively mediate double-bond migrations within unsaturated esters. Once the double-bond is in conjugation with the carboxylate group, they also catalyze the Michael addition of carbon and nitrogen nucleophiles. In the presence of these catalysts, unsaturated carboxylates enter a dynamic equilibrium of positional and geometrical double-bond isomers. The conjugated species are continuously removed through 1,4-additions with formation of β-amino esters or β-arylated products, depending on the nucleophile employed. The applicability of both protocols to a range of substrates, such as fatty esters of different chain lengths and double-bond positions, and several nucleophiles including arylborates and primary and secondary amines, is demonstrated.
机译：发现铑 - 亚磷酸盐催化剂有效地介导不饱和酯中的双键偏移。 一旦双键与羧酸酯基团缀合，它们也催化迈克尔加入碳和氮亲核试剂。 在这些催化剂存在下，不饱和羧酸酯进入位置和几何双键异构体的动态平衡。 通过形成β-氨基酯或β-芳基化产物的形成，连续除去共轭物质，取决于所用的亲核试剂。 对两种方案的适用性在一系列底物中，例如不同链长和双键位置的脂肪酯，以及几种亲核试剂，包括芳族硼酸盐和仲胺，仲胺包括仲胺。

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