EXPERIMENTAL AND THEORETICAL STUDIES ON THE DIASTEREOSELECTIVE DIELS-ALDER REACTIONS OF CHIRAL 1-ALKOXY-1,3-BUTADIENES .1. PARENT SYSTEM AND 4-SUBSTITUTED DERIVATIVES

摘要

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 AMI, have been used in the stereochemical assignment of the adducts. (C) 1997 Elsevier Science Ltd. [References: 37]