title: Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with β-Naphthol or Phenol Derivatives.
abstract: A copper-catalyzed asymmetric [3+2] cycloaddition of 3-trimethylsilylpropargylic esters with either β-naphthols or electron-rich phenols has been realized and proceeds by a desilylation-activated process. Under the catalysis of Cu(OAc)2⋅H2O in combination with a structurally optimized ketimine P,N,N-ligand, a wide range of optically active 1,2-dihydronaphtho[2,1-b]furans or 2,3-dihydrobenzofurans were obtained in good yields and with high enantioselectivities (up to 96 % ee). This represents the first desilylation-activated catalytic asymmetric propargylic transformation.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: Long
authors.initials: L
authors.lastname: Shao
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China.
authors.forename: Ya-Hui
authors.initials: YH
authors.lastname: Wang
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China.|University of Chinese Academy of Sciences, Beijing, 100049, China.
authors.forename: De-Yang
authors.initials: DY
authors.lastname: Zhang
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Xu
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China. xiangping@dicp.ac.cn, xiangping1974@163.com.
authors.forename: Xiang-Ping
authors.initials: XP
authors.lastname: Hu
keywords: asymmetric catalysis; copper; cycloaddition; heterocycles; reaction mechanisms