Tetrahedron

Azetidine based ligands in boron catalyzed asymmetric Diels-Alder reactions

WAJ Starmans, RWA Walgers, L Thijs, R de Gelder…

Index: Starmans, Wim A. J.; Walgers, Richard W.A.; Thijs, Lambertus; De Gelder, Rene; Smits, Jan M.M.; Zwanenburg, Binne Tetrahedron, 1998 , vol. 54, # 19 p. 4991 - 5004

Full Text: HTML

Citation Number: 56

Abstract

The preparation of a new class of azetidine-based auxiliaries and their selectivity in the BBr3 catalyzed Diels-Alder reaction is described. The results are compared with a similar proline- derived ligand and a known prolinol auxiliary. Results show that selectivities are highly dependent on the dienophile and the substituent of the chiral auxiliary.