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
56. S-Alkylation of sulfinamides with Zn-carbenoids: expanding stereoselective sulfoximine synthesis beyond NH derivatives
DOI: 10.1039/D4QO01931H
39. Synthetic Approach toward Enantiopure Cyclic Sulfinamides
20. Stereodivergent Synthesis of Pseudotabersonine Alkaloids
Kazak, M.; Priede, M.; Shubin, K.; Bartrum, H. E.; Poisson, J.-F.; Suna, E. Org. Lett. 2017, 19, 5356–5359.
11. 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. 2014, 79, 3715-3724.
DOI: 10.1021/jo500506u
6. Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of Atropisomeric N–tert-Butanesulfinylketimines
Martjuga, M.; Belyakov, S.; Liepinsh, E.; Suna, E. J. Org. Chem. 2011, 76, 2635–2647.
DOI: 10.1021/jo1025767
5. Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N–tert-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
