A convenient reagent in a modified Curtus reaction for synthesis of carbamates under mild condition without isolating potentially explosive carbonyl azide.1 An azide transfer reagent that effects the coupling of N-acylamino acides or peptides with amino acid or peptide esters without racemization.2 Stereospecific synthesis of azide from alcohols without racemization.3,4 Also used for synthesis of acyl azides from the corresponding N-acyl benzotriazoles,5 Cobalt-catalyzed aziridination of alkenes6 and asymmetric olefins7, transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts8. Use as a reagent recently for crosslinking of collagen biomaterials to increase their resistance to degradation in vivo.9
1. J. Am. Chem. Soc. 1972, 94, 6203.
2. Synlett 2008, 2554.
3. Tetrahedron Lett. 1994, 35, 5081.
4. Org. Synth. 1998, 75, 31.
5. J. Org. Chem. 2007, 72, 5802.
6. J. Org. Chem. 2006, 71, 6655.
7. J. Org. Chem. 2008, 73, 7260.
8. Tetrahedron Lett. 2004, 45, 4241.
9. J. Biomed. Mater. Res. 2003, 67A, 504.