Diastereoselective aza-Michael addition for synthesis of carbohydrate-derived spiropiperazinones

• DOI: 10.1007/s00706-018-2304-x
• Publication Date: 2018-11-15T02:43:53Z
• Authors: Jevgeņija Lugiņina; Deniss Vasiļjevs; Ilgvalds Ivanovs; Anatoly Mishnev; Māris Turks
• Keywords: Michael reaction

3-Deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose reacts with amino acid esters according to the aza-Michael addition pathway. The obtained adducts after reduction of the nitro group spontaneously lactamize and provide novel carbohydrate-derived spiropiperazinones.