Shawn D. Erickson

Enantioselective Complexation with a Conformationally Homogeneous C2 Podand Ionophore

Abstract The podand tetraether 1b has been prepared from (+)-diethyl tartrate. This ionophore is expected to have only one significantly populated conformation. It binds a variety of chiral organic ammonium cations with enantioselectivities corresponding to 34–42% ee.

On the stereochemical control of complexation in tetrahydropyranoid podand ionophores

Abstract To test a proposal that stereochemistry can be used rationally to control the binding properties of ionophores, a new podand (3) has been prepared and studied. Unlike the previously prepared stereoisomeric podand 2 which has substitution and stereochemistry which enforces a single tetradentate binding conformation, 3 has been designed to avoid conformations in which all four oxygens can simultaneously coordinate with an ion.

Enhancing the binding properties of a conformationally rigid podand ionophore

Abstract Stereospecific functionalization of a conformationally rigid podand yields new ionophores having binding properties comparable to those of the macrocyclic crown ethers.