TMSCH2Li-induced regioselective lithiation of (S)-nicotine.
The first regioselective C-4 lithiation of (S)-nicotine has been realized using TMSCH2Li as basic reagent in toluene. The reaction proceeded under mild conditions with a small excess of electrophile. The 4-chloro derivative was subsequently metallated at C-5 with the same basic reagent in THF at -78 degrees C. This methodology opens a straightforward access to functional diversity in (S)-nicotine chemistry.
Gros
Philippe C
PC
Synthèse Organométallique et Réactivité, UMR CNRS-UHP 7565 Université Henri Poincaré, Faculté des Sciences, Boulevard des Aiguillettes, 54506, Vandoeuvre-lès-Nancy, France. philippe.gros@sor.uhp-nancy.fr
Doudouh
Abdelatif
A
Woltermann
Christopher
C
D007202:Indicators and Reagents / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009538:Nicotine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D007202:Indicators and Reagents; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C073196:tetramethylsilane; D009538:Nicotine; D008094:Lithium