78406-16-3Relevant articles and documents
Highly diastereoselective Csp3 -Csp 2 Negishi cross-coupling with 1,2-, 1,3- and 1,4-substituted cycloalkylzinc compounds
Thaler, Tobias,Haag, Benjamin,Gavryushin, Andrei,Schober, Katrin,Hartmann, Evelyn,Gschwind, Ruth M.,Zipse, Hendrik,Mayer, Peter,Knochel, Paul
experimental part, p. 125 - 130 (2010/07/18)
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 Csp3 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.
Montmorillonite clay catalysis. Part 8. Synthesis of arylcholestenes by Friedel-Crafts reaction catalysed by montmorillonite K-10
Li, Li-Jun,Lu, Bo,Li, Tong-Shuang,Li, Ji-Tai
, p. 1439 - 1449 (2007/10/03)
A series of 3β-arylcholestenes were synthesised by Friedel-Crafts reaction of cholesterol with arenes catalysed by montmorillonite K-10.
