Metal-catalyzed asymmetric hetero-DielsAlder reactions of unactivated dienes with glyoxylates

Mogens Johannsen, Sulan Yao, Anette Graven, K. A. Jørgensen
1998 Pure and Applied Chemistry  
The development of a catalytic asymmetric hetero-Diels-Alder methodology for the reaction of unactivated dienes with glyoxylates is presented. Several different asymmetric catalysts can be used, but copper-bisoxazolines and aluminium-BINOL give the highest yield, and the best chemo-and enantioselectivities. The reaction course is dependent on several factors such as the solvent and the anions coordinated to the catalyst. The scope of the reaction is outlined by the total synthesis of a natural occurring actinidiolide.
doi:10.1351/pac199870051117 fatcat:a725mooh4bfehpbgjbiojlqdb4