Weinbender, Thomas and Knierbein, Michael and Bittorf, Lukas and Held, Christoph and Siewert, Riko and Verevkin, Sergey P. and Sadowski, Gabriele and Reiser, Oliver (2020) High-Pressure-Mediated Thiourea-Organocatalyzed Asymmetric Michael Addition to (Hetero)aromatic Nitroolefins: Prediction of Reaction Parameters by PCP-SAFT Modelling. CHEMPLUSCHEM, 85 (6). pp. 1292-1296. ISSN 2192-6506,
Full text not available from this repository. (Request a copy)Abstract
Thiourea-organocatalyzed Michael additions of diethyl malonate to various heteroaromatic nitroolefins (13 examples) have been studied under high-pressure (up to 800 MPa) and ambient pressure conditions. High pressure was conducive to enhanced product yields by a factor of 2-12 at a given reaction time, high reaction rates (reaction times were decreased from 72-24 h down to 4-24 h) and high enantioselectivity. Elucidating the effects of solvents for maximizing reaction rates and yields has been carried out using the Perturbed-Chain Polar Statistical Associating Fluid Theory (PCP-SAFT), allowing for the first time a prediction of the kinetic profiles under high-hydrostatic-pressure conditions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ION-EXCHANGE-RESIN; ACETIC-ACID; CATALYZED ESTERIFICATION; LACTIC-ACID; CHEMICAL-EQUILIBRIUM; COSOLVENT INFLUENCE; REACTION-KINETICS; SOLVENTS; NITROMETHANE; REDUCTION; high-pressure chemistry; kinetics; Michael addition; organocatalysis; thermodynamics |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 22 Mar 2021 12:15 |
| Last Modified: | 22 Mar 2021 12:15 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44458 |
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