Non-biaryl atropisomers derived from carbohydrates. Part 1. Stereoselective synthesis of 1-aryl-5-hydroxyimidazolidine-2-thiones and their transformation into imidazoline-2-thiones

Article abstract of DOI:10.1016/S0040-4020(99)00109-X

A series of chiral-5-hydroxyimidazolidine-2-thiones bearing an ortho- substituted aromatic residue at N-1, which are readily accessible from D- glucosamine, have been synthesized as potential atropisomers. In general, these substances display a trans arrangement between H-4 and H-5, and hence the absolute configuration at C-5 was shown to be R. However, the first example of this type of structures having a cis configuration (S at C-5) is also described. Moreover, the mechanistic features associated with the conversion of 5-acetoxyimidazolidine-2- thiones into imidazoline-2-thiones have also been evaluated.