51431-56-2Relevant academic research and scientific papers
Iron-promoted difunctionalization of alkenes by phenylselenylation/1,2-aryl migration
Wu, Ping,Wu, Kaikai,Wang, Liandi,Yu, Zhengkun
supporting information, p. 5450 - 5453 (2017/11/06)
Iron-promoted difunctionalization of α,α-diaryl and α-aryl-α-alkyl allylic alcohols has been efficiently achieved by means of N-(phenylseleno)phthalimide (N-PSP) under mild conditions. An in situ generated phenylselenium cation (PhSe+) was added to the ol
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.
Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling
Zhang, Ping,Le, Hai,Kyne, Robert E.,Morken, James P.
supporting information; experimental part, p. 9716 - 9719 (2011/08/04)
The Pd-catalyzed cross-coupling of racemic tertiary allylic carbonates and allylboronates is described. This reaction generates all-carbon quaternary centers in a highly regioselective and enantioselective fashion. The outcome of these reactions is consistent with a process that proceeds by way of 3,3′-reductive elimination of bis(η1-allyl)palladium intermediates. Strategies for distinguishing the product alkenes and application to the synthesis of (+)-α-cuparenone are also described.
SELECTIVE REDUCTION OF ALKYNES TO CIS-ALKENES BY HYDROMETALLATION USING 6
Daeuble, John F.,McGettigan, Colleen,Stryker, Jeffrey M.
, p. 2397 - 2400 (2007/10/02)
Selective reduction of alkynes to the corresponding alkenes is reported using the stable, readily prepared copper(I) hydride reagent, 6.Terminal alkynes are reduced at room temperature, unactivated internal alkynes react only at elevated temperature.Disubstituted alkynes with propargyl activation are also reduced, giving cis-olefins selectively.Protection of propargylic alcohol functionality is unnecessary, although fragmentation is sometimes competitive in sterically hindered cases.A tertiary propargyl acetate gave displacement to the allene exclusively.
