title: Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine.
abstract: [reaction: see text] A variety of novel nicotine derivatives were prepared via reductive disilylation of (S)-nicotine. Treatment of nicotine with lithium powder and chlorotrimethylsilane afforded 1,4-bis(trimethylsilyl)-1,4-dihydronicotine in high yield. Addition of various carbonyl electrophiles and a catalytic amount of TBAF provided either C-5 substituted nicotines or 1,4-dihydronicotine derivatives.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA.
authors.forename: Emilie D
authors.initials: ED
authors.lastname: Smith
authors.forename: Florence C
authors.initials: FC
authors.lastname: Février
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Comins
mesh_terms: D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009538:Nicotine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012821:Silanes; D009538:Nicotine; D008094:Lithium