Enantiodifferentiation in taste perception of isovanillic derivatives

Both the enantiomers of three isovanillic chiral 1,3-oxathianes and one 1,3-dithiane were obtained as pure compounds by asymmetric synthesis or chiral HPLC resolution. The absolute configuration was established using X-ray, CD spectra or NMR NOE experiments. The relationships between the structure and the sweet taste of the enantiomeric compounds are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.