Highly stereoselective radical cyclization of haloacetals controlled by the acetal center.
A systematic investigation of radical haloacetal cyclizations (Ueno-Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and gamma-lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)-eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.
Villar
Félix
F
University of Fribourg, Department of Chemistry Pérolles, Switzerland.
Kolly-Kovac
Tanja
T
Equey
Olivier
O
Renaud
Philippe
P