title: Iridium-Catalyzed Intermolecular Asymmetric Dearomatization of β-Naphthols with Allyl Alcohols or Allyl Ethers.
abstract: An Ir-catalyzed intermolecular asymmetric dearomatization reaction of β-naphthols with allyl alcohols or allyl ethers was developed. When an iridium catalyst generated from [Ir(COD)Cl]2(COD=cyclooctadiene) and a chiral P/olefin ligand is employed, highly functionalized β-naphthalenone compounds bearing an all-carbon-substituted quaternary chiral center were obtained in up to 92 % yield and 98 % ee. The direct utilization of allyl alcohols as electrophiles represents an improvement from the viewpoint of atom economy. Allyl ethers were found to undergo asymmetric allylic substitution reaction under Ir catalysis for the first time. The diverse transformations of the dearomatized product to various motifs render this method attractive.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Hang-Fei
authors.initials: HF
authors.lastname: Tu
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Chao
authors.initials: C
authors.lastname: Zheng
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Ren-Qi
authors.initials: RQ
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Xi-Jia
authors.initials: XJ
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China.
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
keywords: allylic substitution; asymmetric catalysis; dearomatization; iridium; naphthol