TMSCH2Li-induced regioselective lithiation of (S)-nicotine
- 24 October 2006
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 4 (23), 4331-4335
- https://doi.org/10.1039/b612786j
Abstract
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 °C. This methodology opens a straightforward access to functional diversity in (S)-nicotine chemistry.Keywords
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