Abstract
The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-,
butane-1,4-, and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate
has been described. A series of cyclic dithioacetals were obtained with yields ranging
from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with
butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation
of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively.
In the case of a cyclic dithioacetal derivative with three methylene groups, a diastereoisomeric
pair of enantiomers was obtained, the structure of which was confirmed by single-crystal
X-ray diffraction analysis. Dithioacetals are useful building blocks in the synthesis
of complex chemical structures. Macrocyclic compounds can be used to complex metal
ions.
Key words
lactic aldehyde - chiral cyclic dithioacetals - scandium triflate - sulfur macrocycle
- dithioacetalization