title: Catalytic Ring Expansion of Cyclic Hemiaminals for the Synthesis of Medium-Ring Lactams.
abstract: A mild and efficient intermolecular ring-expansion approach was developed for the synthesis of medium-ring lactams by using siloxy alkynes. Key to success is the suitable combination of a superior catalyst and an exceptional nitrogen-protecting group. Control experiments indicated that the reaction is remarkably selective toward the desired lactam formation, even with many possible non-productive pathways.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055 (China).|Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China).
authors.forename: Wanxiang
authors.initials: W
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China).
authors.forename: Hui
authors.initials: H
authors.lastname: Qian
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055 (China). lizg@pkusz.edu.cn.
authors.forename: Zigang
authors.initials: Z
authors.lastname: Li
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China). sunjw@ust.hk.
authors.forename: Jianwei
authors.initials: J
authors.lastname: Sun
mesh_terms: D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D007769:Lactams; D009942:Organometallic Compounds
keywords: alkynes; lactams; medium-ring compounds; ring expansion; triflimide