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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 1, pp 21–28 | Cite as

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

  • Jevgeņija LugiņinaEmail author
  • Deniss Vasiļjevs
  • Ilgvalds Ivanovs
  • Anatoly Mishnev
  • Māris Turks
Original Paper
  • 39 Downloads

Abstract

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

Keywords

Carbohydrates Heterocycles Spiro compounds Michael addition Catalytic hydrogenation Lactamization 

Notes

Acknowledgements

The authors thank the Latvian Council of Science Grant no. 10.0030 for materials. The authors thank JSC ‘Olainfarm’ for the kind donation of diacetone-d-glucose. JL thanks the Latvian Academy of Sciences for scholarship.

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied ChemistryRiga Technical UniversityRigaLatvia
  2. 2.Latvian Institute of Organic SynthesisRigaLatvia

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