Chiral sulfinamides are useful templates for asymmetric synthesis due to their unique structural and electronic properties. Ellman’s chiral auxiliary (enantiomerically pure tert-butylsulfinamide) 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 group is focused on developing alternate routes to these compounds via either mixed anhydride approaches or carbodiimide approaches. Using the carbodiimide strategy, we are interested in the preparation of synthesizing a family of α-N-sulfinamido-N-benzylvalinamides as candidates for the organocatalytic reduction of imines and aldehydes. This poster will describe our initial efforts to prepare these compounds by a process of N-sulfinamidation of the benzyl ester of L-valine. This process afforded the desired compound in a non-optimized yield of 53%. The product was chromatographed in hexanes and ethyl acetate (7:3) to afford the individual diastereomers. The late eluting diastereomer was crystalline and this made it possible to determine that this diastereomer was the (SS,S)-diastereomer. From this stage, the synthetic plan is to convert the benzyl ester to a benzyl amide. The product from this transformation would be an N-benzyl-N’-toluenesulfinyl-L-valinamide. This material will ultimately be employed as an organocatalysts in the reduction of aldehydes through the use of diethylzinc, and in the reduction of imines via trichlorosilane.

Developing a synthetic route to S-chiral α-N’-p-toluenesulfinamido-L-valinamides via a carbodiimide approach and application in the asymmetric reduction of aldehydes and imines

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.