55136-52-2Relevant articles and documents
Gas-liquid segmented flow microfluidics for screening copper/tempo-catalyzed aerobic oxidation of primary alcohols
Vanoye, Laurent,Pablos, Mertxe,De Bellefon, Claude,Favre-Réguillon, Alain
, p. 739 - 746 (2015/03/18)
Aerobic oxidation using a combination of copper salts and 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) represent useful tools for organic synthesis and several closely related catalyst systems have been reported. To gain further insights, these catalytic systems were evaluated in a gas-liquid segmented flow device. The improvement of oxygen mass transfer has a significant influence on the turnover-limiting step. Hence, an improved catalytic system using copper(II) as copper source was implemented in a microreactor for the safe and efficient oxidation of primary alcohol.
The conjugate addition-Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands
Iqbal, Mazhar,Duffy, Patricia,Evans, Paul,Cloughley, George,Allan, Bernard,Lledo, Agusti,Verdaguer, Xavier,Riera, Antoni
supporting information; experimental part, p. 4649 - 4661 (2009/03/12)
5-Alkylidenecyclopent-2-enones 15a-q may be prepared via a conjugate addition-Peterson olefination sequence, best achieved in one-pot, using exo-2-trimethylsilyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-one 12, followed by a retro-Diels-Alder reaction. The geometry of the exocyclic alkene may be controlled according to the use of organometallic species in the conjugate addition step; organocuprate reagents are found to selectively lead to the formation of E-exocyclic alkene adducts, whereas Grignard reagents favour the formation of Z-alkenyl isomers. The use of enantiomerically enriched 12, accessed from an asymmetric Pauson-Khand reaction, affords the corresponding enantioenriched 5-alkylidenecyclopent-2-enones and this approach is exemplified by the short, stereoselective total syntheses of two cyclopentenone phytoprostanes 51 and 13,14-dehydrophytoprostane J165. The ability of this family of synthetic compounds to activate the peroxisome proliferator activated receptor-γ is reported.
A new method for oxidation of various alcohols to the corresponding carbonyl compounds by using n-t-butylbenzenesulfinimidoyl chloride
Matsuo, Jun-Ichi,Iida, Daisuke,Tatani, Kazuya,Mukaiyama, Teruaki
, p. 223 - 234 (2007/10/03)
Various primary and secondary alcohols were smoothly oxidized to the corresponding aldehydes and ketones by using a new oxidizing agent, N-t-butylbenzenesulfinimidoyl chloride (4a), in the coexistence of DBU or zinc oxide. The present oxidation proceeded under mild conditions via five-membered intramolecular proton-transfer of an alkyl arenesulfinimidate intermediate.