Synthesis of C-4 Substituted Nicotine Derivatives via an N-Acylpyridinium Salt of (S)-Nicotine
- 28 September 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (22) , 5059-5062
- https://doi.org/10.1021/ol0520469
Abstract
A variety of novel nicotine derivatives were prepared from (S)-nicotine via a two-step sequence. Addition of a cuprate reagent to an N-acylpyridinium salt of nicotine, followed by aromatization with elemental sulfur, afforded C-4 substituted nicotines in moderate to high yield. Using this method, 4-(dimethylphenylsilyl)nicotine was prepared and oxidized to afford (S)-4-hydroxynicotine.Keywords
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