Categories: C-N Bond Formation > Synthesis of azides >
Synthesis of β-azidoketones
Recent Literature
A chiral (salen)Al complex catalyzes the highly enantioselective conjugate
addition of carbon- and nitrogen-based nucleophiles to various acyclic α,β-unsaturated
ketones providing access to a wide range of useful chiral building blocks in
high yield and enantiomeric excess.
M. S. Taylor, D. N. Zalatan, A. M. Lerchner, E. N. Jacobsen, J. Am. Chem. Soc.,
2005,
127, 1313-1317.
Amberlite IRA900N3 is an excellent and recyclable organocatalyst
for the azidation of α,β-unsaturated ketones with trimethylsilyl azide under
solvent-free conditions. This procedure is a green tool for the preparation
of β-azido ketones under mild conditions with good yields.
L. Castrica, F. Fringuelli, L. Gregoli, F. Pizzo, L. Vaccaro, J. Org. Chem., 2006,
71, 9536-9539.
A mild oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium
nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides β-functionalized
ketones in short reaction times. This method provides an alternative
pathway to important starting materials and intermediates in organic synthesis.
J. Jiao, L. X. Nguyen, D. R. Patterson, R. A. Flowers II, Org. Lett., 2007,
9, 1323-1326.
