期刊
NATURE CHEMISTRY
卷 2, 期 2, 页码 125-130出版社
NATURE PORTFOLIO
DOI: 10.1038/NCHEM.505
关键词
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资金
- European Research Council
- Fonds der Chemischen Industrie
- Sonderforschungsbereich [749]
- Deutsche Forschungsgemeinschaft
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.
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