Direct Catalytic Enantioselective Conjugate Addition of α-Substituted Benzyl Nitriles to Alkyl Acrylates
作者:Sadhanendu Samanta、Jin Cui、Yasunari Otsuka、Takumi Watanabe、Masakatsu Shibasaki
DOI:10.1021/acs.orglett.4c00427
日期:2024.3.22
The first enantioselective copper-catalyzed conjugate addition of α-substituted benzyl nitriles to alkyl acrylates is described. This protocol allows the direct and 100% atom-economic generation of a nitrile-containing quaternary stereogenic center in a highly enantioselective manner. The practical application of our methodology was demonstrated through the concise formal synthesis of (−)-aphanorphine
描述了α-取代的苄基腈与丙烯酸烷基酯的第一个对映选择性铜催化共轭加成反应。该方案允许以高度对映选择性的方式直接且 100% 原子经济地生成含腈的四元立体中心。我们的方法的实际应用通过 (−)-aphanorphine 的简明形式合成得到了证明。