α,α,α′,α′‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols (TADDOLs) for Resolutions of Alcohols and as Chiral Solvating Agents in NMR Spectroscopy

Abstract

AbstractThe use of α,α,α′,α′ ‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols ( = TADDOLs;1) as chiral NMR shift reagents (1H, 13C, 19F) is described. In many cases, the ratio of enantiomeric alcohols and amines can be determined under standard conditions of measurement (CDCl3 as solvent, room temperature). The preparation and use of a new type of TADDOL, the tetrakis(dimethylamino) derivative 1d, is described. Menthol, octan‐2‐ol, and oct‐1‐yn‐3‐ol are partially resolved by crystallization of clathrates with 1c and 1d.