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

Reiter C, Lopez-Molina S, Schmid B, Neiß C, Görling A, Tsogoeva S (2014)


Publication Language: English

Publication Type: Journal article, Original article

Publication year: 2014

Journal

Original Authors: Reiter C., Lopez-Molina S., Schmid B., Neiss C., Gorling A., Tsogoeva S.B.

Publisher: Wiley-VCH Verlag

Book Volume: 6

Pages Range: 1324-1332

Journal Issue: 5

DOI: 10.1002/cctc.201301052

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.

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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://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.

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