Tandem reverse-electron-demand Diels-Alder reactions of 1,5-cyclooctadiene

Article abstract of DOI:10.1016/S0040-4039(00)92688-1

Hexachlorocyclopentadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-2,4-diene react with 1,5-cyclooctadiene to produce a 1:4 syn to anti mixture of diadducts in good yield. The stereochemistry of the diastereomers is examined using X-ray and molecular mechanics calculations are used to explore some of the potential causes for the observed diastereoselectivity.