SYNTHESIS OF THREE NEW BIFUNCTIONAL GLUCOSE-THIOUREA ORGANOCATALYSTS AND THEIR APPLICATION IN ASYMMETRIC MICHAEL ADDITION
Date
2017-03-30
Authors
Sándor NAGY
Petra KOZMA
Péter KISSZÉKELYI
Dóra BEZZEGH
Péter HUSZTHY
József KUPAI
Journal Title
Journal ISSN
Volume Title
Publisher
STUDIA UBB CHEMIA. Published by Babeş-Bolyai University
Abstract
Three new glucose-based asymmetric bifunctional organocatalysts containing a 6-aminopyridyl or a 6-methylpyridyl or a cinchona unit were synthesized. Asymmetric Michael addition of pentane-2,4-dione to β-nitrostyrene was catalyzed successfully by these catalysts. In case of the cinchona based glucose-thiourea derivate the S enantiomer of the corresponding Michael adduct was formed with moderate enantiomeric excess in three different solvents.
Description
STUDIA UBB CHEMIA, LXII, 1, 2017 (p. 183-194), DOI:10.24193/subbchem.2017.1.16
Sándor NAGY
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary, nagy.sandor@mail.bme.hu
https://orcid.org/0000-0001-6251-5382
Petra KOZMA
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Péter KISSZÉKELYI
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary, pkisszekelyi@mail.bme.hu
https://orcid.org/0000-0002-9529-0674
Dóra BEZZEGH
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Péter HUSZTHY
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary, huszthy@mail.bme.hu
https://orcid.org/0000-0002-3652-9892
József KUPAI
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
*Corresponding author: jkupai@mail.bme.hu
https://orcid.org/0000-0002-4212-4517
Keywords
organocatalyst, carbohydrates, cinchona alkaloids, Michael addition, asymmetric syntheses
Citation
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