Chiral polyamino alcohols via hydroaminomethylation: A new class of polyamines for dendritic cores and ligand precursors

Abstract

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. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.