N,N′-(1S)-[1,1′-Binaphthalene]-2,2′-diylbis-(2S,2′S)-pyrrolidine-2-carboxamide

Abstract

[891496-34-7] C30H30N4O2 (MW 478.24) InChI = 1S/C30H30N4O2/c35-29(25-11-5-17-31-25)33-23-15-13-19-7-1-3-9-21(19)27(23)28-22-10-4-2-8-20(22)14-16-24(28)34-30(36)26-12-6-18-32-26/h1-4,7-10,13-16,25-26,31-32H,5-6,11-12,17-18H2,(H,33,35)(H,34,36) InChIKey = FYTHJMKJVUTERE-UHFFFAOYSA-N (used as a catalyst and as a ligand in enantioselective synthesis of aldol products and cyanosilylation of kentones, respectively) Alternate Names: (Sa)-2,2′-bis[((2S)-pyrrolidin-2-ylcarbonyl)amino]-1,1′-binaphthalene, (S)-Binam-l-Pro. Physical Data: mp 230 °C; (c = 1, MeOH). Solubility: soluble in most polar organic solvents; insoluble in hexane, ether, and water. Form Supplied in: not commercially available. Prepared from (Sa)-2,2′-diamino-1,1′-binaphthalene and protected l-proline, both commercially available. Analysis of Reagent Purity: elemental analysis, NMR, HRMS, and X-ray structure. Preparative Methods: the reagent can be prepared by coupling (Sa)-2,2′-diamino-1,1′-binaphthalene with the mixed anhydride obtained from l-Boc-proline and isobutyl or ethyl chloroformate or by direct coupling of Boc-L-proline with (Sa)-2,2′-diamino-1,1′-binaphthalene (Binam) mediated by 1-ethyl-3-(3-methylaminopropyl)carbodiimide (EDC) and 1-hydroxybenzotriazole (HOBt) or N,N′-dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). The coupled intermediate was deprotected by using TFA. Alternatively, the reagent can be prepared by coupling (Sa)-2,2′-diamino-1,1′-binaphthalene with the acyl chloride derived from Fmoc-l-proline, and deprotection with piperidine. Purification: by column chromatography and/or recrystallization from CH2Cl2/hexane or CHCl3/ether. Handling, Storage, and Precaution: the reagent is stable for months when stored in air at room temperature.