Michael addition of N-unprotected 2-oxindoles to nitrostyrene catalyzed by bifunctional tertiary amines: Crucial role of dispersion interactions

Journal article
(Original article)


Publication Details

Author(s): Reiter C, Lopez-Molina S, Schmid B, Neiß C, Görling A, Tsogoeva S
Journal: ChemCatChem
Publisher: Wiley-VCH Verlag
Publication year: 2014
Volume: 6
Journal issue: 5
Pages range: 1324-1332
ISSN: 1867-3880
Language: English


Abstract


Bifunctional thiourea- or sulfonamide-derived tertiary amines catalyze the enantioselective nitro-Michael addition of N-unprotected 3-substituted 2-oxindoles to nitrostyrene in up to 99 % yields, 94:6 er, and 87:13 dr. Overcoming the necessity to introduce and remove activating or protecting groups at the nitrogen moiety leads to a reduction of energy use, costs, and waste. Transition-state geometries for the formation of all possible stereoisomers in the nitro-Michael addition of N-unprotected 3-substituted 2-oxindole to nitrostyrene catalyzed by Takemoto's tertiary amine-thiourea are calculated. It is shown that the relative positions and binding patterns of the reactants and the catalyst molecule are largely determined by van der Waals interactions. The importance of being dispersed: Bifunctional thiourea- or sulfonamide-derived tertiary amines such as Takemoto's catalyst catalyze the enantioselective nitro-Michael addition of N-unprotected 3-substituted 2-oxindoles to nitrostyrene in high yields and enantiomeric and diastereomeric ratios. DFT calculations including van der Waals corrections are performed for the stereoisomers. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.



FAU Authors / FAU Editors

Görling, Andreas Prof. Dr.
Lehrstuhl für Theoretische Chemie
Neiß, Christian Dr.
Lehrstuhl für Theoretische Chemie
Schmid, Bernhard
Lehrstuhl für Theoretische Chemie
Tsogoeva, Svetlana Prof. Dr.
Professur für Organische Chemie


How to cite

APA:
Reiter, C., Lopez-Molina, S., Schmid, B., Neiß, C., Görling, A., & Tsogoeva, S. (2014). Michael addition of N-unprotected 2-oxindoles to nitrostyrene catalyzed by bifunctional tertiary amines: Crucial role of dispersion interactions. ChemCatChem, 6(5), 1324-1332. https://dx.doi.org/10.1002/cctc.201301052

MLA:
Reiter, Christoph, et al. "Michael addition of N-unprotected 2-oxindoles to nitrostyrene catalyzed by bifunctional tertiary amines: Crucial role of dispersion interactions." ChemCatChem 6.5 (2014): 1324-1332.

BibTeX: 

Last updated on 2019-06-04 at 21:50