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.
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
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
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.
