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Improvements and Applications of the Transition Metal‐Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates
Author(s) -
Grassi David,
Alexakis Alexandre
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500495
Subject(s) - chemistry , stereocenter , tsuji–trost reaction , magnesium , reagent , alkylation , transition metal , allylic rearrangement , combinatorial chemistry , catalysis , grignard reagent , enantioselective synthesis , organic chemistry
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.