An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels-Alder reactions

DP Heller, DR Goldberg, H Wu…

Index: Heller, Douglas P.; Goldberg, Daniel R.; Wu, Hongqiao; Wulff, William D. Canadian Journal of Chemistry, 2006 , vol. 84, # 10 p. 1487 - 1503

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Citation Number: 23

Abstract

Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels-Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6-and 6'-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4-and 4'-positions. The set of four ...