@misc{comins_fevrier_smith_2007, title={Regioselective halogenation of nicotine and substituted nicotines}, volume={7,179,917}, number={2007 Feb. 20}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Fevrier, F. and Smith, E. D.}, year={2007} } @misc{comins_fevrier_smith_2006, title={Regioselective halogenation of nicotine and substituted nicotines}, volume={7,067,672}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Comins, D. L. and Fevrier, F. and Smith, E. D.}, year={2006} } @article{smith_fevrier_comins_2006, title={Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine}, volume={8}, ISSN={["1523-7052"]}, DOI={10.1021/ol052099q}, abstractNote={[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.}, number={2}, journal={ORGANIC LETTERS}, author={Smith, ED and Fevrier, FC and Comins, DL}, year={2006}, month={Jan}, pages={179–182} } @article{comins_kuethe_miller_fevrier_brooks_2005, title={Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones}, volume={70}, ISSN={["0022-3263"]}, DOI={10.1021/jo050559n}, abstractNote={Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels-Alder cyclization with various dienophiles to afford novel octahydroquinolines containing synthetically useful functionality. With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtained as single diastereomers in good to excellent yield. The corresponding reaction of 5 with methyl acrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts. The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial control was examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxin was prepared in a stereocontrolled fashion. Interesting reactivity was observed with certain dienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reaction provides a route to uniquely substituted beta-aminoketones, alcohols, and unnatural amino acids.}, number={13}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Kuethe, JT and Miller, TM and Fevrier, FC and Brooks, CA}, year={2005}, month={Jun}, pages={5221–5234} } @article{fevrier_smith_comins_2005, title={Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives}, volume={7}, ISSN={["1523-7052"]}, DOI={10.1021/ol052196j}, abstractNote={[reaction: see text] Regioselective deprotonations of (S)-nicotine and derivatives at the C-2 and C-6 positions of the pyridine ring were performed in good to excellent yields. These methodologies allow the direct introduction of a plethora of functional groups onto the pyridine ring of nicotine.}, number={24}, journal={ORGANIC LETTERS}, author={Fevrier, FC and Smith, ED and Comins, DL}, year={2005}, month={Nov}, pages={5457–5460} } @article{comins_king_smith_fevrier_2005, title={Synthesis of C-4 substituted nicotine derivatives via an N-acylpyridinium salt of (S)-nicotine}, volume={7}, ISSN={["1523-7060"]}, DOI={10.1021/ol0520469}, abstractNote={[reaction: see text] 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.}, number={22}, journal={ORGANIC LETTERS}, author={Comins, DL and King, LS and Smith, ED and Fevrier, FC}, year={2005}, month={Oct}, pages={5059–5062} }