title: One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties.
abstract: We successfully expand the application of lactols or cyclic hemiaminals as nucleophiles for the asymmetric synthesis of both N,O- and N,N-acetal moieties contained in the structure of ring-fused piperidine derivatives. This efficient one-pot protocol involves an organocatalyzed asymmetric aza-Diels-Alder reaction and iminium ion induced cyclization sequence to ultimately deliver heterocyclic compounds with excellent stereoselectivity in high yield, containing three continuous stereogenic centers.
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
authors.forename: Ji-Yao
authors.initials: JY
authors.lastname: Li
authors.affiliation: School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, P. R. China. liuyankai@ouc.edu.cn.
authors.forename: Zhi-Long
authors.initials: ZL
authors.lastname: Li
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
authors.forename: Wei-Wei
authors.initials: WW
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
authors.forename: Yan-Kai
authors.initials: YK
authors.lastname: Liu
authors.affiliation: School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, P. R. China. liuyankai@ouc.edu.cn.
authors.forename: Zhi-Ping
authors.initials: ZP
authors.lastname: Tong
authors.affiliation: School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, P. R. China. liuyankai@ouc.edu.cn.
authors.forename: Rui
authors.initials: R
authors.lastname: Tan