First Example of the Intermolecular Palladium-Catalyzed Asymmetric Allylic Alkylation of Hydroxyacrylates: Synthesis of All-Carbon α-Aryl Quaternary Aldehydes
First Example of the Intermolecular Palladium-Catalyzed Asymmetric Allylic Alkylation of Hydroxyacrylates: Synthesis of All-Carbon α-Aryl Quaternary Aldehydes
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DOI：
10.1002/ejoc.201402911
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发表时间：
2014-09-01
影响因子：
2.8
通讯作者：
Hossain, M. Mahmun
中科院分区：
文献类型：
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作者：
Asad, Sharif A.;Ulicki, Joseph;Hossain, M. Mahmun
通过分子间钯催化的不对称烯丙基烷基化反应（Pd-AAA）合成了一系列无环全碳α-芳基季醛。羟基丙烯酸酯被用作前所未有的亲核对应物，而不是广泛使用的酮底物。这产生了非常罕见的全碳季醛。发现手性配体（R，R）-L3在该Pd-AAA反应中是最佳的，并且与一系列类似物一起提供良好至优异的产率（75-99%）和对映选择性（75-94%）。
A set of acyclic all-carbon alpha-aryl quaternary aldehydes was synthesized by intermolecular palladium-catalyzed asymmetric allylic alkylation (Pd-AAA). Hydroxyacrylates were used as unprecedented nucleophilic counterparts instead of widely used ketone substrates. This produced a very rare all-carbon quaternary aldehyde. Chiral ligand (R, R)-L3 was found to be optimal in this Pd-AAA reaction and provided good to excellent yields (75-99%) and enantioselectivities (75-94%) with a range of analogs.