Experimental and theoretical studies on the diastereoselective Diels-Alder reactions of chiral 1-alkoxy-1,3-butadienes. I: Parent system and 4-substituted derivatives

Article abstract of DOI:10.1016/S0040-4020(97)00854-5

Chiral 1-alkoxy-1,3-dienes (parent and 4-substituted) have been prepared from the corresponding chiral alkoxyacetylenes in a stereoselective manner following a 2C + 2C approach. The Diels-Alder reactions of the dienes with maleic anhydride and 4-phenyl-3H-1,2,4-triazoline-3,5-dione take place with significant diastereoselectivity. Theoretical calculations on these cycloadditions, performed with the SCF-MO procedure AM1, have been used in the stereochemical assignment of the adducts.