The preparation of enantiopure building blocks is a fundamental area of importance for synthetic chemistry. We became particularly interested in asymmetric ring opening of sylilcyclopentene oxides with different nucleophiles such as azide and acetate using Jacobsen's catalysts. Silylcyclopentene oxide is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol triol-azide and triol-amines. The sequences employed allow for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold. We have now turned our attention towards utilizing bifunctional substrates containing two cyclopentene oxide rings as an attempt to double the molar output of these reactions, while reducing the waste created by spectator ligands. It turns out that the two asymmetric transformations work independent of the other functional groups present on the substrate and high enantioselectivity and good yield was achieved. This type of atom economy has other applications to multiplying catalytic output using other polyfunctional substrates.