69498-77-7Relevant academic research and scientific papers
Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan
Hsu,Fang
, p. 8573 - 8584 (2007/10/03)
By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.
Regiospecific Metallation in Palladium-Hydrazone Complexes
Galli, Beatrice,Gasparrini, Francesco,Maresca, Luciana,Natile, Giovanni,Palmieri, Gianni
, p. 1483 - 1488 (2007/10/02)
The dimethylhydrazone of pinacolone, ButMeC=N1N2Me2, reacts with (R = Me or Ph) to give the complexes tMeC=NNMe2)2> and tMeC=NNMe2)>2>, in which the ligands co-ordinat
GENERATION OF DIENONE AND TRIENONE DIANION DERIVATIVES; DOUBLE DEPROTONATION AS A ROUTE TO LUMO-FILLED ?-SYSTEMS
Seebach, Dieter,Pohmakotr, Manat
, p. 4047 - 4058 (2007/10/02)
Conjugated unsaturated carbonyl compounds and their analogues 1 are a1,3,5...-reagents.An umpolung of this intrinsic reactivity can be achieved by generation of the dianions 2, LUMO filled ?-systems, from hydrogenated precursors, see schemes 1
