State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering , Lanzhou University , 222 South Tianshui Road , Lanzhou 730000 , China.
J Am Chem Soc. 2019 May 8;141(18):7637-7643. doi: 10.1021/jacs.9b03863. Epub 2019 Apr 25.
Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase in molecular diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids.
对映选择性交叉亲电反应仍然是金属催化中的一个具有挑战性的课题,就数据而言,研究主要集中在手性中心转化的外消旋烷基亲电试剂的反应上。在这里,我们报告了一种非活化烯烃的对映选择性交叉亲电芳基-烯丙基化反应。该方法可用于合成许多具有生物重要性的手性分子,如二氢苯并呋喃、吲哚啉和茚满。引入的烯基适合进一步反应,可以增加分子的多样性和复杂性。反应在温和条件下于室温下进行,使用易于获得的手性吡咯烷配体,可以获得具有高对映选择性的产物。该方法的合成实用性通过能够修饰复杂分子如肽、吲哚美辛和甾体化合物得到了证明。