Diastereoselective Synthesis of Cycloalkylamines by Samarium Diiodide-Promoted Cyclizations of α-Amino Radicals Derived from α-Benzotriazolylalkenylamines
JM Aurrecoechea, B López, A Fernández…
Index: 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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Citation Number: 29
Abstract
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 ...
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