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. 2008 Apr 3;10(7):1381-4.
doi: 10.1021/ol703071c. Epub 2008 Mar 4.

Proximity-assisted cycloaddition reactions--facile Lewis acid-mediated synthesis of diversely functionalized bicyclic tetrazoles

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Proximity-assisted cycloaddition reactions--facile Lewis acid-mediated synthesis of diversely functionalized bicyclic tetrazoles

Stephen Hanessian et al. Org Lett. .

Abstract

Aliphatic azidonitriles separated by three or four carbon atoms undergo facile Lewis acid-induced cycloadditions to give bicyclic tetrazoles, even at 0 degrees 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 thermodynamically controlled enantiopure products proceeding through discrete oxocarbenium ion intermediates.

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