5729-53-3Relevant articles and documents
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
Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes
Pelter,Smith,Elgendy
, p. 7119 - 7132 (2007/10/02)
In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, the Z-alkenes may result predominantly, particularly in the cases of R(S)CHO and R(t)CHO.