Categories: C-N Bond Formation > Synthesis of azides >
Synthesis of 1,2-azido alcohols
Recent Literature
An efficient ring opening of epoxides and aziridines has been carried out at
room temperature using poly(ethylene glycol) (PEG-400) as reaction medium to
form the corresponding 2-azido alcohols and 2-azido amines, respectively, in
excellent yields within 30-45 minutes and with high regio- and stereoselectivity.
B. Das, V. S. Reddy, F. Tehseen, M. Krishnaiah, Synthesis, 2007,
666-668.
A wide variety of epoxides and aziridines were converted to the
corresponding β-azido alcohols and β-azido amines with sodium azide using
Oxone® in aqueous acetonitrile. The reactions were highly regioselective and
efficient with excellent yields at room temperature under mild reaction
conditions.
G. Sabitha, S. R. Babu, M. S. K. Reddy, J. S. Yadav, Synthesis,
2002, 2254-2258.
A convenient, efficient, and highly regioselective synthesis of 1,2-azidoalcohols and 1,2-azidoamines in excellent
yields has been achieved by using cerium(III) chloride and
sodium azide for a mild ring opening of epoxides and aziridines.
G. Sabitha, R. S. Babu, M. Rajkumar, J. S. Vadav, Org.
Lett., 2002, 4, 343-345.
In an efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins
for synthesis of β-azido alcohols, an aerobic oxidative generation of azido
radical is a key process. The reaction offers broad substrate scope, the use of
an inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild
conditions at room temperature.
X. Sun, X. Li, S. Song, Y. Zhu, Y.-F. Liang, N. Jiao, J. Am. Chem. Soc., 2015,
137, 6059-6066.
A readily prepared N3-iodine(III) reagent acts as a clean N3-radical
precursor in a radical azidooxygenation of various alkenes in the presence of
TEMPONa as a mild organic reducing reagent. The C-radical generated after N3-radical
addition is efficiently trapped by in situ generated TEMPO. Yields are very
good, and for cyclic systems azidooxygenation occurs with excellent
diastereoselectivity.
B. Zhang, A. Studer, Org. Lett., 2013,
15, 4548-4551.
Aldehydes are safely and conveniently converted to acyl azides and benzyl
ethers to azido ethers by treatment with polymer supported iodine azide in MeCN
at 83 °C. The reaction provides an alternative to the use of iodine azide in
radical azidonations.
L. G. Marinescu, C. M. Pedersen, M. Bols, Tetrahedron, 2005,
61, 123-127.
Related
Lipase-catalyzed enantioselective esterification of β-azido alcohols in
combination with ruthenium-catalyzed alcohol isomerization enables a successful
dynamic kinetic resolution (DKR) of racemic β-azido alcohols to the
corresponding enantiomerically pure acetates.
O. Pàmies, J.-E. Bäckvall, J. Org. Chem., 2001,
66, 4022-4025.