63296-63-9Relevant academic research and scientific papers
O-DPPB-directed copper-mediated and -Catalyzed allylic substitution with grignard reagents
Demel, Peter,Keller, Manfred,Breit, Bernhard
, p. 6669 - 6683 (2008/09/16)
The ortho-diphenylphosphanylbenzoyl (o-DPPB) group was explored as a directing leaving group in copper-mediated and copper-catalyzed allylic substitution with Grignard reagents. Complete control of chemo-, regio- and stereoselectivity with complete syn-1,3-chirality transfer was observed as a result of the directed nature of the reaction. No excess of or ganometallic reagent is required and the directing group can be recovered quantitatively. Coordination studies in the solid state and in solution have shown that two substrates are bound via the phosphine function of the directing group at copper. Dynamic NMR experiments in solution are in agreement with a ligand-exchange process at copper, a prerequisite for the development of a substoichiometric process.
Synthetic applications of functionalized silyl anions: Aminosilyl anions as hydroxy anion equivalent
Tamao, Kohei,Kawachi, Atsushi,Tanaka, Yoko,Ohtani, Hitoshi,Ito, Yoshihiko
, p. 5765 - 5772 (2007/10/03)
An (aminosilyl)lithium and the corresponding copper and magnesium reagents serve as a hydroxy anion equivalent through (1) allylic substitution, (2) addition to vinyloxirane, and (3) addition to acetylene, followed by oxidative cleavage of the silicon-carbon bonds. Highly regio- and stereoselective transformations have been achieved in all cases.
Sulfonic peracids - III. Heteroatom oxidation and chemoselectivity
Kluge,Schulz,Liebsch
, p. 5773 - 5782 (2007/10/03)
We have investigated the p-toluenesulfonic peracid (2) generated in situ in the oxidation of different types of compounds containing nitrogen and/or sulfur. The sulfonic peracid 2 shows a remarkable chemoselectivity characterized by a preferred oxidation of sulfides to the sulfones in the presence of amines or olefins and a strong dependence on the nature of the amine in the competitive oxidation of olefins and amines.
