Proximity-Assisted Cycloaddition Reactions Facile Lewis Acid-Mediated Synthesis of Diversely Functionalized Bicyclic Tetrazoles

S Hanessian, D Simard, B Deschênes-Simard…

Index: Hanessian, Stephen; Simard, Daniel; Deschenes-Simard, Benoit; Chenel, Caroline; Haak, Edgar Organic Letters, 2008 , vol. 10, # 7 p. 1381 - 1384

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Citation Number: 15

Abstract

Aliphatic azidonitriles separated by three or four carbon atoms undergo facile Lewis acid- induced cycloadditions to give bicyclic tetrazoles, even at 0° C. Extension to 3-azido-2-aryl- 1, 3-dioxolanes and the corresponding 1, 3-dioxanes in the presence of TMSCN and BF3⊙ OEt2 leads to a series of diversely functionalized novel oxabicyclic tetrazoles. The reactions represent new aspects of proximity-assisted dipolar cycloadditions that afford ...