title: Regioselective nucleophilic addition of organometallic reagents to 3-geminal bis(silyl) N-acyl pyridinium.
abstract: A regioselective nucleophilic addition to 3-geminal bis(silyl) N-acyl pyridinium has been described. Geminal bis(silane) shows contrasting roles that lead to different regioselectivities for the addition of different nucleophiles: its steric effect dominates to favor 1,6-addition of alkyl, vinyl, and aryl organometallic reagents; its directing effect dominates to favor 1,2-addition of less sterically demanding alkynyl Grignard reagents.
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, ‡State Key Laboratory of Biotherapy, West China Hospital, §Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610041, P. R. China.
authors.forename: Ya
authors.initials: Y
authors.lastname: Wu
authors.forename: Linjie
authors.initials: L
authors.lastname: Li
authors.forename: Hongze
authors.initials: H
authors.lastname: Li
authors.forename: Lu
authors.initials: L
authors.lastname: Gao
authors.forename: Hengmu
authors.initials: H
authors.lastname: Xie
authors.forename: Zhigao
authors.initials: Z
authors.lastname: Zhang
authors.forename: Zhishan
authors.initials: Z
authors.lastname: Su
authors.forename: Changwei
authors.initials: C
authors.lastname: Hu
authors.forename: Zhenlei
authors.initials: Z
authors.lastname: Song
mesh_terms: D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011726:Pyridinium Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D011726:Pyridinium Compounds; D012821:Silanes