Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine.
[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.
Smith
Emilie D
ED
Department of Chemistry, North Carolina State University, Raleigh, 27695-8204, USA.
Février
Florence C
FC
Comins
Daniel L
DL
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
D012821:Silanes; D009538:Nicotine; D008094:Lithium