Categories: C-N Bond Formation > Amines > Amino Alcohols
Synthesis of γ-amino alcohols
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An aza-Michael addition-asymmetric transfer hydrogenation tandem process
provides chiral γ-secondary amino alcohols in high yields with high
enantioselectivities. This one-pot tandem process involves an aza-Michael
addition of aryl-substituted enones and amines to form aryl-substituted
γ-secondary amino ketones, followed by a Ru-catalyzed asymmetric transfer
hydrogenation.
L. Wu, R. Jin, L. Li, X. Hu, T. Cheng, G. Liu, Org. Lett.,
2017, 19, 3047-3050.
Intramolecular C-H amination using commercial Rh-catalysts, PhI(OAc)2, and MgO offers a practical solution for the controlled oxidation of saturated C-H
bonds. Reactions of sulfamates with 2 mol % Rh2(OAc)4,
PhI(OAc)2, and MgO yield selectively six-membered ring oxathiazinanes.
These heterocycles can serve as precursors for 1,3-amino alcohols, β-amino
acids, and numerous other amine derivatives.
C. G. Espino, P. M. Wehn, J. Chow, J. Du Bois, J. Am. Chem. Soc., 2001,
123, 6935-6936.