手性选择性的 Pd 催化的非环 1,3-二烯与活化亲核试剂的分子间氢烷基化反应。
Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.
机构信息
Department of Chemistry, Duke University , Durham, North Carolina 27708, United States.
出版信息
J Am Chem Soc. 2018 Feb 28;140(8):2761-2764. doi: 10.1021/jacs.7b13300. Epub 2018 Feb 20.
Abstract
We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.
摘要
我们报告了一种高对映选择性的 Pd-PHOX 催化的非环 1,3-二烯的分子间氢烷基化反应。Meldrum's 酸衍生物和其他活化的 C-亲核试剂，如β-二酮和丙二腈，与各种芳基和烷基取代的二烯在室温下反应 20 小时内即可完成。所得到的偶联产物，最高产率可达 96%，对映选择性可达 97.5:2.5，很容易转化为用于下游合成的有用的化学构建块。
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