Harris Michael R, Konev Mikhail O, Jarvo Elizabeth R
Department of Chemistry, University of California , Irvine, California 92697-2025, United States.
J Am Chem Soc. 2014 Jun 4;136(22):7825-8. doi: 10.1021/ja5026485. Epub 2014 May 23.
Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both π-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective synthesis of a polycyclic furan is demonstrated.
对映体富集的亚甲基环戊烷是通过仲苄基醚的立体专一性、镍催化的Heck环化反应合成的。该反应对π-扩展芳烃和简单芳烃的苄基醚均以高产率和对映体专一性进行。带有1,2-二取代烯烃侧链的醚形成三取代烯烃，同时控制绝对构型和烯烃几何形状。展示了多环呋喃的非对映选择性合成。
