Diastereoselective Synthesis of Cycloalkylamines by Samarium Diiodide-Promoted Cyclizations of α-Amino Radicals Derived from α-Benzotriazolylalkenylamines

JM Aurrecoechea, B López, A Fernández…

文献索引：Aurrecoechea, Jose M.; Lopez, Beatriz; Fernandez, Alvaro; Arrieta, Ana; Cossio, Fernando P. Journal of Organic Chemistry, 1997 , vol. 62, # 4 p. 1125 - 1135

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被引用次数: 29

摘要

The condensation of ω-unsaturated aldehydes with benzotriazole and secondary amines affords α-benzotriazolylalkenylamines that exist in solution as mixtures of the corresponding benzotriazol-1-yl and benzotriazol-2-yl isomers resulting from their rapid dissociation into iminium cations and the benzotriazolyl anion. The reduction of these adducts with samarium diiodide (SmI2) takes place with formation of the benzotriazolyl anion and α-amino alkenyl ...