Nornicotine aqueous aldol reactions: synthetic and theoretical investigations into the origins of catalysis

…, T Lovell, MM Meijler, L Noodleman…

Index: Dickerson, Tobin J.; Lovell, Timothy; Meijler, Michael M.; Noodleman, Louis; Janda, Kim D. Journal of Organic Chemistry, 2004 , vol. 69, # 20 p. 6603 - 6609

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Citation Number: 63

Abstract

The recent discovery that nornicotine 1, a minor nicotine metabolite, can catalyze the aldol reaction under physiologically relevant conditions has initiated research efforts into the potential chemical roles of nicotine metabolites. Herein, we disclose studies aimed at determining the origin and thus mechanism of the nornicotine-catalyzed aqueous aldol reaction. Conformationally constrained compounds designed to mimic the low-energy ...