Proximity-assisted cycloaddition reactions - Facile Lewis acid-mediated synthesis of diversely functionalized bicyclic tetrazoles
(Chemical Equation Presented) 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 thermodynamically controlled enantiopure products proceeding through discrete oxocarbenium ion intermediates.
Hanessian, Stephen,Simard, Daniel,Deschenes-Simard, Benoit,Chenel, Caroline,Haak, Edgar
body text
p. 1381 - 1384
(2009/04/18)
More Articles about upstream products of 5817-87-8