Ellman’s sulfinamide (enantiomerically enriched tert-butylsulfinamide) has been at the forefront of much of the chemistry of the chiral sulfinamides due to its versatility in the synthesis of chiral amines, beta-amino alcohols, and amino acids among other compounds. The Ellman auxiliary is used primarily as a stoichiometric agent for diastereoselective reactions, but there is an increasing use of such compounds as chiral organocatalysts in enantioselective reactions such as reduction, epoxide opening, and the Strecker synthesis. Chiral sulfinamides are often prepared from sulfinyl chlorides with a chiral agent that promotes dynamic kinetic resolution for the isolation of diastereomerically pure sulfinate esters. Our research program is focused on developing alternate routes to these compounds via either mixed anhydride approaches or carbodiimide approaches. Ultimately, we are interested in developing these routes as asymmetric preparative methods for sulfinamides for use in the process of asymmetric opening of meso-epoxides. This poster will describe our initial efforts to prepare a series of phenoxy sulfinate esters bearing different substituents that will allow the probing of impact of structural and electronic properties on the process of dynamic kinetic resolution. Ultimately, we are interested in developing phenoxy sulfinate esters as more easily prepared and more stable surrogates for sulfinyl chlorides. The poster will discuss our efforts to refine the coupling method for the preparation of phenoxy sulfinate esters and their use in the process of dynamic kinetic resolution.<br/>

Synthesis and development of phenoxy sulfinate esters as tools for the synthesis of chiral sulfinamides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.