Iron(M) Chloride As An Efficient Catalyst For Stereoselective Synthesis Of Glycosyl Azides And A Cocatalyst With Cu(0) For The Subsequent Click Chemistry!

摘要

A highly efficient and mild method for azido glycosylation of glycosyl p-peracetates to 1,2-trans glycosyl azides was developed by using inexpensive FeCI^ as the catalyst. In addition, we demonstrated, for the first time, that FeCl3 in combination with copper powder can promote 1,3-dipoIar cycloaddition (click chemistry) of azido glycosides with terminal alkynes. Good to excellent yields were obtained with exclusive formation of a single isonier in both glycosyl azidation and subsequent cycloaddition processes.