66004-20-4Relevant academic research and scientific papers
Ring-opening of cyclic ethers with carbon-carbon bond formation by Grignard reagents
Christensen, Stig Holden,Holm, Torkil,Madsen, Robert
, p. 4942 - 4946 (2014/07/07)
The ring-opening of cyclic ethers with concomitant C-C bond formation was studied with a number of Grignard reagents. The transformation was performed in a sealed vial by heating to ～160 °C in an aluminum block or at 180 °C in a microwave oven. Good yields of the product alcohols were obtained with allyl- and benzylmagnesium halides when the ether was tetrahydrofuran or 3,3-dimethyloxetane. Lower yields were obtained with substituted tetrahydrofurans while no ring-opening was observed with tetrahydropyran. Only highly reactive allyl and benzyl Grignard reagents participated in the transformation while no reaction occurred with other alkylmagnesium halides.
Enantioselective α-arylation of aldehydes via organo-SOMO catalysis. An ortho-selective arylation reaction based on an open-shell pathway
Conrad, Jay C.,Kong, Jongrock,Laforteza, Brian N.,MacMillan, David W. C.
supporting information; experimental part, p. 11640 - 11641 (2009/12/08)
(Chemical Equation Presented) The intramolecular-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pendent electron-rich aromatics and heterocycles thus efficiently providing cyclic α-aryl aldehyde products (10 examples: ≥70% yield and ≥90% ee). In accordance with our radical mechanism, when there is a choice between arylation at the ortho or para position of anisole substrates, we find that arylation proceeds selectively at the ortho position.
Synthesis and stereochemical studies: Chemical and catalytic reductions of a new class of dihydropyrrole and tetrahydropyridine derivatives
Ghosh, Arindam,Bhattacharya, Sudin,Raychaudhuri, S. R.,Chatterjee, Amreshwar
, p. 299 - 309 (2007/10/02)
Tetrahydropyridine derivatives 1g,h on catalytic (PtO2/H2) or hydride (LAH or NaBH4) reductions afford stereoselectively the corresponding cis-amines 20a,b.Catalytic reduction of the dihydropyrrole derivative 1e gives a complex material; while NaBH4 reduc
AROMATIC ANNULATION WITH BISPHENYLTHIONIUM IONS
Manas, Abdul Rahman Bin,Smith, Robin A. J.
, p. 1847 - 1856 (2007/10/02)
The chemospecific production and intramolecular aromatic electrophilic substitution (annulation) of bis(phenylthio)carbocations (bisphenylthionium ions) has been studied using appropriate model compounds.The annulation reaction is very sensitive to the Lewis acid initiator and also the solvent.The best reaction conditions were found to be a suspension of silver trifluoromethanesulfonate in dichloromethane.Annulation of six-membered rings onto alkylbenzene and five- and seven-membered rings onto activated benzenes have been achieved.
