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Catalytic Enantioselective ?-selective Addition Of 2-allylazaarenes To Activated Ketones

Posted on:2018-01-08Degree:MasterType:Thesis
Country:ChinaCandidate:X B BaiFull Text:PDF
GTID:2321330518469195Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Azaarenes containing an embedded imine(C=N)exhibit electron-withdrawing properties,which have allowed 2-alkylazaarenes as nucleophiles and 2-alkenylazaarenes as electrophiles in catalytic enantioselective reactions to access valuable ?-and/or ?-functionalized chiral azaarenes.Herein,we report the first example of 2-allylazaarenes in asymmetric catalysis.Highly ?-selective allylation was demonstrated for activated ketones,including isatins and trifluoromethyl ketones.In the presence of amino acid-based tertiary amine or quaternary ammonium salt catalyst,two series of tertiary hydroxyl-containing biologically potential scaffolds were installed at the remote ?-position of azaarenes in good chemical yields,excellent enantioselectivities and E/Z ratios.The success of current ?-selective reactions should provide inspiration for expansion to other allylazaarene derivatives and would open up new paradigms for the synthesis of chiral ?-and/or ?-functionalized azaarenes.
Keywords/Search Tags:Asymmetric Organocatalysis, 2-Allylic Azaarenes, ?-Selectivity, ?-Functionalization, Allylation Reactions
PDF Full Text Request
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