Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation
作者:Qiaozhi Yan、Guiying Xiao、Ying Wang、Guofu Zi、Zhanbin Zhang、Guohua Hou
DOI:10.1021/jacs.8b12657
日期:2019.1.30
A highly efficient and enantioselective Rh-( R, R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-( R, R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[ b]thiophene-1,1-dioxides
已开发出一种高效且对映选择性的 Rh-( R, R)-f-spiroPhos 络合物催化氢化一系列不饱和砜。在温和条件下使用 Rh-( R, R)-f-spiroPhos 催化剂,不仅首次实现了 3,3-二芳基和环外 α,β-不饱和砜的不对称氢化,ee 高达 99.9%,而且 3 -烷基-3-芳基和苯并[b]噻吩-1,1-二氧化物成功氢化成相应的手性砜,具有优异的对映选择性(高达99.4% ee),而不受底物的空间位阻、电子性质和几何形状的影响. 此外,该反应提供了将 (S)-(+)- ar-turmerone 作为香料的途径,这是一种重要的药物合成中间体。