Thaler, Tobias and Haag, Benjamin and Gavryushin, Andrei and Schober, Katrin and Hartmann, Evelyn and Gschwind, Ruth M. and Zipse, Hendrik and Mayer, Peter and Knochel, Paul (2010) Highly diastereoselective Csp(3)-Csp(2) Negishi cross-coupling with 1,2-, 1,3-and 1,4-substituted cycloalkylzinc compounds. NATURE CHEMISTRY, 2 (2). pp. 125-130. ISSN 1755-4330,
Full text not available from this repository. (Request a copy)Abstract
Stereoselective functionalizations of organic molecules are of great importance to modern synthesis. A stereoselective preparation of pharmaceutically active molecules is often required to ensure the appropriate biological activity. Thereby, diastereoselective methods represent valuable tools for an efficient set-up of multiple stereocentres. In this article, highly diastereoselective Csp(3) Negishi cross-couplings of various cycloalkylzinc reagents with aryl halides are reported. In all cases, the thermodynamically most-stable stereoisomer was obtained. Remarkably, this diastereoselective coupling was successful not only for 1,2-substituted cyclic systems, but also for 1,3- and 1,4-substituted cyclohexylzinc reagents. The origin of this remote stereocontrol was investigated by NMR experiments and density functional theory calculations. A detailed mechanism based on these experimental and theoretical data is proposed.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PALLADIUM-CATALYZED REACTION; SECONDARY ALKYL-HALIDES; STEREOSELECTIVE PREPARATION; ORGANOZINC REAGENTS; GRIGNARD-REAGENTS; NICKEL-COMPLEXES; BASIS-SET; CARBON; BROMIDES; DENSITY; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 10 Aug 2020 08:46 |
| Last Modified: | 10 Aug 2020 08:46 |
| URI: | https://pred.uni-regensburg.de/id/eprint/25238 |
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