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

…, T Lovell, MM Meijler, L Noodleman…

文献索引：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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被引用次数: 63

摘要

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 ...