Jr. Mcelhanon et Dv. Mcgrath, Toward chiral polyhydroxylated dendrimers. Preparation and chiroptical properties, J ORG CHEM, 65(11), 2000, pp. 3525-3529
Four dendrimers (1b-4b) containing chiral vicinal diol-based subunits were
prepared from their acetonide-protected precursors (1a-4a). The optical act
ivity of these chiral dendritic structures was successfully modeled using s
tructurally similar, low molecular weight model compounds. Using the [Phi](
d) values of the low molecular weight model compounds 5b-7b, we calculated
[Phi](d) values for dendrimers 1b-4b that agree to within 4.5% of the obser
ved values. Agreement between the optical activity of the model compounds a
nd that of the dendrimers leads to the conclusion that the conformational e
quilibria of the dendrimer subunits are not perturbed relative to those of
the model compounds.