title: Catalytic Asymmetric Construction of α-Quaternary Cyclopentanones and Its Application to the Syntheses of (-)-1,14-Herbertenediol and (-)-Aphanorphine.
abstract: A novel and efficient strategy to build α-benzylic quaternary cyclopentanones with excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 % yield) has been developed, and its application demonstrated by the first catalytic asymmetric total synthesis of (-)-1,14-herbertenediol and the formal synthesis of (-)-aphanorphine.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P. R. China), Fax: (+86) 931-8912582.
authors.forename: Dao-Yong
authors.initials: DY
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P. R. China), Fax: (+86) 931-8912582.
authors.forename: Ming-Hui
authors.initials: MH
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P. R. China), Fax: (+86) 931-8912582. tuyq@lzu.edu.cn.
authors.forename: Yong-Qiang
authors.initials: YQ
authors.lastname: Tu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P. R. China), Fax: (+86) 931-8912582.
authors.forename: Fu-Min
authors.initials: FM
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P. R. China), Fax: (+86) 931-8912582. wangshh@lzu.edu.cn.|School of Pharmacy, Lanzhou University, and Key Laboratory of Drug, Targeting and Drug Delivery System, Ministry of Education, Sichuan University, Chengdu (P. R. China). wangshh@lzu.edu.cn.
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Wang
keywords: asymmetric synthesis; enantioselectivity; organocatalysis; quaternary stereocenters; sesquiterpenes