128900-82-3Relevant academic research and scientific papers
Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates
Grassi, David,Alexakis, Alexandre
supporting information, p. 3171 - 3186 (2015/11/03)
Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.
Copper-free asymmetric allylic alkylation with grignard reagents
Jackowski, Olivier,Alexakis, Alexandre
supporting information; experimental part, p. 3346 - 3350 (2010/07/15)
(Chemical Equation Presented) Open wide and say AAA: The copper-free asymmetric allylic alkylation reaction of Crignard reagents, catalyzed by N-heter-ocyclic carbenes, is reported for allyl bromide derivatives. This reaction offers good enantioselectivit
Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS+
Matsumoto, Kouichi,Fujie, Shunsuke,Suga, Seiji,Nokami, Toshiki,Yoshida, Jun-Ichi
supporting information; experimental part, p. 5448 - 5450 (2009/12/08)
A catalytic amount of electrochemically generated "ArS +" ("ArS+" = ArS(ArSSAr)+) initiates a cation chain reaction of dienes that involves the addition of ArSSAr associated with stereoselective intramolecular carbon-carbon bond formation, and the direct (in-cell) electrolysis of a mixture of a diene and ArSSAr with a catalytic amount of electricity also effectively initiates the reaction. The Royal Society of Chemistry 2009.
Rh-catalyzed enantioselective diboration of simple alkenes: Reaction development and substrate scope
Trudeau, Stephane,Morgan, Jeremy B.,Shrestha, Mohanish,Morken, James P.
, p. 9538 - 9544 (2007/10/03)
The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.
Intramolecular anodic olefin coupling reactions: A useful method for carbon-carbon bond formation
Hudson, Christine M.,Marzabadi, Mohammad R.,Moeller, Kevin D.,New, Dallas G.
, p. 7372 - 7385 (2007/10/02)
The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The e
