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Synthesis of 1,2-amino alcohols


Name Reactions

Sharpless Aminohydroxylation

Recent Literature

Effective hydrolysis of epoxides and aziridines was conducted in water at 60 or 100°C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. Hot water acts as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.
Z. Whang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem., 2008, 73, 2270-2274.

A N-heterocyclic carbene serves as an efficient catalyst for the regioselective ring-opening reactions of aziridines in the presence of acid anhydrides to afford the desired products in good to excellent yields.
X. Sun, S. Ye, J. Wu, Eur. J. Org. Chem., 2006, 4787-4790.

The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene gave carboxylates of 1,2-amino alcohols. A plausible mechanism for this reaction is discussed.
Y.-K. Liu, R. Li, L. Yue, B.-J. Li, Y.-C. Chen, Y. Wu, L.-S. Ding, Org. Lett., 2006, 8, 1521-1524.

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.

Pd-catalyzed selective oxidation of Boc-protected N-methylamines with IOAc as the oxidant involves a Boc-directed C-H activation process.
D.-H. Wang, X.-S. Hao, D.-F. Wu, J.-Q. Yu, Org. Lett., 2006, 8, 3387-3390.


A highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.
T.-X. Métro, D. G. Pardo, J. Cossy, J. Org. Chem., 2007, 72, 6556-6561.

N,N-Dialkyl-β-amino alcohols derived from α-amino acids can be rearranged enantiospecifically by using TFAA/Et3N/NaOH to give 1,2-amino alcohols.
T.-X. Métro, J. Appenzeller, D. G. Pardo, J. Cossy, Org. Lett., 2006, 8, 3509-3512.

The use dynamic kinetic resolution combined with asymmetric transfer hydrogenation in water provides β-hydroxy-α-(tert-butoxycarbonyl)amino esters in good yields, diastereoselectivities, and enantioselectivities. A surfactant is employed to achieve good yields due to the hydrophobic nature of both the catalyst and substrate.
B. Seashore-Ludlow, F. Seint-Dizier, P. Somfai, Org. Lett., 2012, 14, 6334-6337.