首页|Enantioselective Synthesis of α-Alkenylated γ-Lactam Enabled by Ni-Catalyzed 1,4-Arylcarbamoylation of 1,3-Dienes
Enantioselective Synthesis of α-Alkenylated γ-Lactam Enabled by Ni-Catalyzed 1,4-Arylcarbamoylation of 1,3-Dienes
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The facile construction of chiral quaternary α-alkenylated pyrrolidinones is a long-term challenge in organic synthesis.The asymmetric difunctionaliza-tion of 1,3-dienes represents the most compelling tool for assembling alkenylated compounds by regiose-lective 1,2-or 1,4-difunctionalization.Nevertheless,the manipulation of unactivated 1,3-dienes to forge the quarternary stereogenic center still remains large-ly underdeveloped.Herein,we disclose a nickel-catalyzed asymmetric 1,4-arylcarbamoylation of unactivated 1,3-dienes tethered on carbamoyl fluo-ride with readily available arylboronic acids,provid-ing rapid access to the enantioenriched α-alkenylated pyrrolidinones bearing the quaternary stereogenic center in high yields with broad functional group tolerance.Moreover,this chiral ligand-controlled asymmetric transformation overcomes the intrinsic substrate control with a preexisting chiral center.
lactamnickel13-dieneenantioselective dicarbofunctionalizationquaternary stereogenic center
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering,Feringa Nobel Prize Scientist Joint Research Center,Frontiers Science Center for Materiobiol-ogy and Dynamic Chemistry,School of Chemistry and Molecular Engineering,East China University of Science and Technology,Shanghai 200237
国家自然科学基金上海市自然科学基金Shanghai Rising-Star Program上海市科技计划重大项目Program of Introducing Talents of Discipline to Universities中央高校基本科研业务费专项中国博士后科学基金
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