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Issue 23, 2006
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TMSCH2Li-induced regioselective lithiation of (S)-nicotine

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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.

Graphical abstract: TMSCH2Li-induced regioselective lithiation of (S)-nicotine

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Publication details

The article was received on 04 Sep 2006, accepted on 10 Oct 2006 and first published on 24 Oct 2006


Article type: Paper
DOI: 10.1039/B612786J
Org. Biomol. Chem., 2006,4, 4331-4335

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    TMSCH2Li-induced regioselective lithiation of (S)-nicotine

    P. C. Gros, A. Doudouh and C. Woltermann, Org. Biomol. Chem., 2006, 4, 4331
    DOI: 10.1039/B612786J

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