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Highly efficient, multigram and enantiopure synthesis of (S)-2-(2,4′-bithiazol-2-yl)pyrrolidine |
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| Authors: | Xavier Just-Baringo Paolo Bruno Fernando Albericio Mercedes Álvarez |
| Institution: | a Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona, Baldiri Reixac 10, E-08028 Barcelona, Spain b CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, E-08028 Barcelona, Spain c Department of Organic Chemistry, University of Barcelona, E-08028 Barcelona, Spain d Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, E-08028 Barcelona, Spain |
| Abstract: | (S)-2-(4-Bromo-2,4′-bithiazole)-1-(tert-butoxycarbonyl)pyrrolidine ((S)-1) was obtained as a single enantiomer and in high yield by means of a two-step modified Hantzsch thiazole synthesis reaction when bromoketone 3 and thioamide (S)-4 were used. Further conversion of (S)-1 into trimethyltin derivative (S)-2 broadens the scope for further cross-coupling reactions. |
| Keywords: | Hantzsch cyclization Thiazole Thiopeptides Proline |
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