Diastereoselective aza-Michael Addition for Synthesis of Carbohydrate-Derived Spiropiperazinones

Monatshefte fur Chemie 2019
Jevgeņija Lugiņina, Deniss Vasiļjevs, Ilgvalds Ivanovs, Anatolijs Mišņovs, Māris Turks

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. Graphical abstract: [Figure not available: see fulltext.].

Keywords
Carbohydrates, Catalytic hydrogenation, Heterocycles, Lactamization, Michael addition, Spiro compounds
DOI
10.1007/s00706-018-2304-x
Hyperlink
https://link.springer.com/article/10.1007%2Fs00706-018-2304-x

Lugiņina, J., Vasiļjevs, D., Ivanovs, I., Mišņovs, A., Turks, M. Diastereoselective aza-Michael Addition for Synthesis of Carbohydrate-Derived Spiropiperazinones. Monatshefte fur Chemie, 2019, Vol.150, No.1, pp.21-28. ISSN 0026-9247. e-ISSN 1434-4475. Available from: doi:10.1007/s00706-018-2304-x

Publication language
English (en)