Chiral sulfinamides are useful templates for asymmetric synthesis due to their unique structure and electronic properties. Ellman’s chiral auxiliary has been at the forefront of much of the chemistry of the sulfinamides due to its versatility in the synthesis of chiral amines, beta-amino alcohols, and amino acids. The Ellman auxiliary is used primarily as a stoichiometric agent for diastereoselective reactions, but there is an increasing use of such compounds as chiral catalysts in enantioselective alkylations, and reductions. Chiral sulfinamides are most often prepared from chiral sulfinyl chlorides. 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. This poster will describe our initial efforts to prepare p-tolylsulfinamides based on oxazolidinones, oxazolidine-2-thiones, and oxadiazinones using the EDC coupling method. The poster will also cover our efforts to refine the coupling method with a series of achiral amines and anilines. Finally, the poster will cover our work on the synthesis of chiral sulfinamides derived from reaction with alpha-amino esters derived from alanine, phenylalanine, and valine.

Carbodiimide approach to the synthesis of chiral alpha-amino ester sulfinamides

255th National Meeting (2018)

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