Structure-Dependent Nickel-Catalysed Transposition of N-Allylamides to E- or Z-Enamides
Structure-Dependent Nickel-Catalysed Transposition of N-Allylamides to E- or Z-Enamides
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DOI：
10.1055/s-0036-1588340
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发表时间：
2016-11
期刊：
影响因子：
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通讯作者：
F. Weber;Philipp S. Steinlandt;Monika Ballmann;G. Hilt
中科院分区：
文献类型：
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作者：
F. Weber;Philipp S. Steinlandt;Monika Ballmann;G. Hilt
本文报道了镍催化的N-烯丙基酰胺和N-高烯丙基酰胺的碳-碳双键转位反应。虽然非环状酰胺的转座得到了非常高的Z-选择性的烯酰胺，相应的环状N-烯丙基酰胺导致专门的E-配置的产品。因此，我们实现了一种依赖于酰胺取代基结构的烯酰胺的立体分散方法。当使用高烯丙基底物时，可以实现在低温下温度控制的单转座为Z-烯丙基酰胺衍生物或在高温下双转座为E-烯酰胺。
Abstract The nickel-catalysed transposition of a carbon–carbon double bond of N-allyl and N-homoallyl amides is described. While the transposition of acyclic amides gave very high Z-selectivity of the enamides, corresponding cyclic N-allyl amides led exclusively to the E-configured products. Thereby, we realised a stereodivergent approach to enamides that is dependent on the structure of the amide substituents. When homoallylic substrates are used, a temperature-controlled single transposition to a Z-allylic amide derivative at low temperature or a double transposition to an E-enamide at elevated temperature could be achieved.