Chiral solute–solvent systems. Selective interaction between N-dodecanoyl-L-valine amides and N-trifluoroacetyl esters of the enantiomers of 2-aminoalkan-1-ols and α-, β-, and γ-amino-acids

Abstract

Optically active 2-aminoalkan-1-ols in the form of their O-acyl-N-trifluoroacetyl derivatives have been resolved by g.l.c. with N-dodecanoyl-L-valine 6-undecylamide (1) as the stationary phase. A bulky O-acyl group substantially facilitates resolution. Resolutions of the N-trifluoroacetyl-esters of α-, β-, and γ-amino-acids on diamide phases are also reported. The order of emergence of the derivatives of the 2-aminoalkan-1-ols and the γ-amino-acids is D after the L-isomer, i.e., the reverse of that found for the α-amino-acids.

The mechanism of resolution is discussed on the basis of association complexes involving the formation of two hydrogen bonds between the solutes and the solvent.