Chiral Polyamino Alcohols via Hydroaminomethylation: A New Class of Polyamines for Dendritic Cores and Ligand Precursors

In this contribution, the synthesis of a new class of chiral polyamino alcohols (PAA) via a two-step hydroaminomethylation/hydrolysis procedure is reported. The chiral polyamines are obtained by hydroaminomethylation of N-olefinic oxazolidinones with different amines in first step followed by hydrolysis of the resulting polyamines to give the chiral PAA in the second step. The dendritic chiral PAA (Mw = 1300-1400 g mol(-1)) are also synthesized efficiently through a multifold hydroaminomethylation/hydrolysis procedure. Furthermore, chiral PAA are investigated as ligands in ruthenium-catalyzed asymmetric hydrogen transfer reduction of acetophenone to 1-phenyl alcohol.