Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam,Useful Intermediate for the Synthesis of Bioactive Compounds |
| |
| Authors: | Roberta Listro Giacomo Rossino Serena Della Volpe Rita Stabile Massimo Boiocchi Lorenzo Malavasi Daniela Rossi Simona Collina |
| |
| Institution: | 1.Department of Drug Sciences, University of Pavia, via Taramelli 12, 27100 Pavia, Italy; (R.L.); (G.R.); (S.D.V.); (R.S.); (S.C.);2.Centro Grandi Strumenti, University of Pavia, via Bassi 21, 27100 Pavia, Italy;3.Department of Chemistry, University of Pavia, via Taramelli 12, 27100 Pavia, Italy; |
| |
| Abstract: | During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams. |
| |
| Keywords: | lactam scaffold enantioselective HPLC chiral resolution X-ray diffraction absolute configuration assignment |
|
|
