Amino-alcohols hydroxyamines

The reaction between epoxides and ammonia is a general and useful method for the preparation of P-hydroxyamines. " Ammonia gives largely the primary amine, but also some secondary and tertiary amines. The useful solvents, the ethanolamines, are prepared by this reaction. For another way of accomplishing this conversion, see 10-54. The reaction can be catalyzed with Yb(OTf)3 and in the presence of a-BINOL is l,l -bi-2-naphthol derivative gives amino alcohols with high asymmetric induction. A variation used Yb(OTf)3 at lOkbar or at ambient pressure. Lithium triflate can also be used. Primary and secondary amines give, respectively, secondary and tertiary amines, for example. 

Aminoalcohols(Hydroxyamines Alcamines or Alkanolamines) contain both die amino- and the hydroxyl groups attached to different C atoms, usually adjacent, such as monoethanolamine or 2-aminoethanol HOCHa CHa NH, diethanolamine or 2,2 -iminodiethanol (HOCH2 Qia )2 NH and triethanolamine (HOCHa CHa )jN. Many amino alcohols and their derivs are important products of commerce and some of them serve for the prepn of expls... 

Aza-allyl anions also react with carbonyl derivatives to give iV-protected P-hydroxyamines and p-amino alcohols after reduction or hydrolysis.334... 

Table 8. Auxiliary-Induced Osmium Catalyzed Hydroxyamination Reactions / -Hydroxy Carbamates 1 and /5-Amino Alcohols 293...

Also, A-hydroxy- 3-amino alcohols 44 (R = H, Scheme 4.6) were achieved in high yields and enantioselectivities using axially chiral secondary amine catalyst 46a (10 mol%) to perform the hydroxyamination of linear aldehydes 42 with nitrosobenzene (43a, Ar=Ph), with excellent results (77-90%, 97-99% ee) [45]. Due to the instability of the resulting hydroxyamination product, in situ reduction to the corresponding alcohol was carried out using NaBH. ... 

Sulfotransferases (SULTs) are cytosolic phase II detoxification enzymes involved in sulfonation of various xenobiotics and endobiotics. There are also membrane-bound SULTs that are not involved in phase II metabolism but are involved in the sulfonation of proteins and polysaccharides. Substrates of cytosolic SULTs include alcohols (ethanol, 2-butanol, cholesterol, bile acids), phenols (phenol, naphthol, acetaminophen), aromatic amines and hydroxyamines (2-naphthylamine, A-hydroxy 2-naphthylamine). SULTs transfer sulfonate (S03) to a hydroxy or amino group of a substrates from the cofactor 3 -phosphoadenosine-5 -phosphosulfate (PAPS), generating highly water-soluble metabolites for elimination through the kidney and liver. 

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