941570-75-8Relevant 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.
Construction of enantioenriched cyclic compounds by asymmetric allylic alkylation and ring-closing metathesis
Giacomina, Francesca,Alexakis, Alexandre
, p. 6710 - 6721 (2013/11/06)
A new approach to highly enantioenriched cyclic compounds (up to 98a€‰% ee) has been developed by using ω-ethylenic allylic substrates in a one-pot asymmetric allylic alkylation and ring-closing metathesis sequence. The starting compounds are synthetic equivalents of cyclic allylic substrates. The method is exemplified with both Cu and Ir catalysts, and chiral phosphoramidite ligands. A new approach to highly enantioenriched cyclic compounds (up to 98a€‰% ee) has been developed by using ω-ethylenic allylic substrates in a one-pot asymmetric allylic alkylation and ring-closing metathesis sequence. The starting compounds are synthetic equivalents of cyclic allylic substrates. The method is exemplified with both Cu and Ir catalysts, and chiral phosphoramidite ligands. Copyright
Bidentate hydroxyalkyl NHC ligands for the copper-catalyzed asymmetric allylic substitution of allyl phosphates with grignard reagents
Magrez, Magaly,Le Guen, Yann,Basle, Olivier,Crevisy, Christophe,Mauduit, Marc
supporting information, p. 1199 - 1203 (2013/02/25)
Demonstrating their potential: Bidentate alkoxy NHC ligands have been used in the copper-catalyzed asymmetric allylic alkylation of allyl phosphates with Grignard reagents (see scheme). The method provides access to tertiary and quaternary chiral centers with high regio- and enantioselectivity. The system is also applied to the synthesis of chiral E,E-dienes, a key structural motif prevalent in natural products. Copyright
ω-Ethylenic allylic substrates as alternatives to cyclic substrates in copper- and iridium-catalyzed asymmetric allylic alkylation
Giacomina, Francesca,Riat, David,Alexakis, Alexandre
supporting information; experimental part, p. 1156 - 1159 (2010/05/18)
"Chemical Equation Presented" A new strategy to access highly enantioenriched cyclic compounds (up to 98%) Is proposed using ω-ethylenic allylic substrates through a one-pot asymmetric allylic alkylation and ring-closing metathesis. Such starting compounds can be seen as synthetic equivalents of cyclic allylic substrates.
