Synthesis of 1,2-azido alcohols
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.
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.