Abstract

In many ways, water is an ideal solvent: it is cheap, abundant, renewable, non-toxic, and non-flammable, making it the prime alternative to the organic solvents used in chemical reactions. Unfortunately, the water insolubility of most organic compounds limits its use as a solvent. Significant progress has been made in micellar catalysis, in which organic reactions take place in the organic medium in the interior of the micelle. We report our progress in creating micelles that contain immobilized catalysts capable of catalyzing reactions within the interior of the micelle and are able to be immediately recycled without any purification or isolation, similar to catalysts immobilized to solid phase surfaces. Specifically, we synthesized a derivative of a currently produced steroidal surfactant, SPGS-550-M. This derivative contains a Proline derivative linked to the D-ring of the steroid in place of the β-sitosterol side-chain present in SPGS-550-M. We hypothesize that this new surfactant, 24, when mixed with SPGS-550-M in water, will generate micelles capable of stereoselectively catalyzing reactions through the interaction of starting materials with the Proline derivative. Future work will demonstrate not only the ability to catalyze the reactions but also the ability to reuse the micelles and characterize the micelles by dynamic light scattering (DLS), cryo-TEM, and pulse-field gradient (PFG) NMR.