83440-17-9Relevant academic research and scientific papers
Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis
Chen, Shuming,Han, Feng,Houk, K. N.,Ivlev, Sergei,Meggers, Eric,Xie, Xiulan,Ye, Chen-Xi
, p. 13552 - 13556 (2020/06/05)
A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 percent yield and with up to >99.5 percent ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.
SYNTHESE D'ALDEHYDES γ-FONCTIONNELS PAR VOIE RADICALAIRE
Filliatre, Claude,Baratchart, Michel,Villenave, Jean-Jacques,Jaouhari, Rabih
, p. 3487 - 3488 (2007/10/02)
The addition of radicals issued from the solvent to the double bond of O,O-t-butyl and O-vinyl peroxycarbonate results on the free-radical induced decomposition of this peroxyester and offers an original synthetic route for γ-functional aldehydes.
Obtention d'aldehydes γ-fonctionnels au cours de la thermolyse du percarbonate de O,O-t-butyle et O-vinyle en solution
Filliatre, Claude,Villenave, Jean-Jacques,Jaouhari, Rabih,Baratchart, Michel
, p. 352 - 356 (2007/10/02)
Owing to its peroxyester group, O,O-tert-butyl and O-vinyle peroxycarbonate may act as a free radical initiator in solution, but also, due to the presence of the vinylic insaturation, as a substrate for free radical addition reactions. - In such solvents as cumene which give free radicals unable to add to the double bond, the peroxycarbonate merely behaves as a vinyloxy radicals generator.It is thus possible to observe these radicals reacting either as formylmethyl radicals or as acetyl radicals. - In solvents such as cyclohexane which give free radicals able to add to the double bond, the reaction results in the substitution of formylmethyl groups to labile hydrogens of the solvent. - By applying the reaction to such compounds as ketones, ethers, acids and their derivatives, we could obtain γ-functional aldehydes (γ-ketoaldehydes, γ-oxaaldehydes and derivatives of succinaldehydic acids).These products are often difficult to prepare by other routes and until now only some of them have been described.
