Efficient preparation of polymer-supported enantiopure chiral aminoalcohols via phenolic spacers

Derivatives of protected phenols with chiral aminoalcohol or aminoether-containing substituents in the 4-position of the aromatic ring were prepared and shown to react readily, after deprotection, with chloromethylated styrene-divinylbenzene polymers. The chirality in the substituents originated either from the use of a chiral monomeric aminoalcohol derivative or from the introduction of a chiral epoxide, which in turn was ring opened by a chiral amine. The chiral epoxides were obtained by either asymmetric synthesis or starting from a chiral glycidyl derivative.