Diastereoselective synthesis using Ellman’s chiral auxiliary

Many pharmacologically relevant chemical compounds contain chiral amine functionality. Therefore the development of stereoselective methods for synthesis of chiral, non-racemic amines is of high importance in organic and pharmaceutical chemistry. Stereoselective synthesis employing Ellman’s chiral tert-butanesulfinamide reagent is among the most efficient ways to prepare chiral amines.

We are interested in the application of Ellman’s N-tert-butanesulfinyl chiral auxiliary in the development of new synthetic methods to access amines with multiple stereogenic centers.

 

Publications:

3. “Diastereoselective Hydroxymethylation of Cyclic N-tert-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source”, Priede, M.; Kazak, M.; Kalnins, T.; Shubin, K.; Suna, E. J. Org. Chem. 201479, 3715-3724. DOI: 10.1021/jo500506u

JOC_2014_1

2. “Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of Atropisomeric Ntert-Butanesulfinylketimines”, Martjuga, M.; Belyakov, S.; Liepinsh, E.; Suna, E. J. Org. Chem. 2011, 76, 2635–2647. DOI: 10.1021/jo1025767

JOC_2_TOC

1. “Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure Ntert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent”, Martjuga, M.; Shabashov, D.; Belyakov, S.; Liepinsh, E.; Suna, E. J. Org. Chem. 2010, 75, 2375-2368. DOI: 10.1021/jo100173f