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Synthesis Of Chiral Schiff Base N,O-ligands And Its Preliminary Application In Henry Reaction

Posted on:2015-01-04Degree:MasterType:Thesis
Country:ChinaCandidate:X Y ZuoFull Text:PDF
GTID:2251330428483730Subject:Chemical Engineering and Technology
Abstract/Summary:PDF Full Text Request
This paper mainly studied the synthesis of14chiral schiff base N,O-ligands bysimple method, and the reduction of ligand L15by chiral ligand L1with sodiumborohydride. All15synthesized chiral ligands have been characterized by NMR, Anduse these15chiral N, O-ligands with metal complexes of copper salt forming appliedto asymmetric Henry reactions.The structure of the designed Chiral ligands were, The part of amine isR-(+)-α-phenethylamine, S-(-)-α-2-naphthalene ethyl amine; The part of aldehyde isreplacing salicylaldehyde. The Ligands of L1-L14synthesis at the condition:0.02mol amine and0.02mol aldehyde, with10mL anhydrous ethanol as solvent, refluxafter4h, natural cooling, quiet place for the night, recrystallization. To restore ligandsL1, under low temperature, the partial join sodium borohydride reductant, high yieldof the reduction product.The application of15chiral ligands in asymmetric Henry reaction was carriedout in the preliminary exploration, discovery of such chiral ligands in various types ofnitromethane asymmetric Henry reaction of aldehydes showed some hand inductionability, when use the ligand L7, copper triflate copper precursor, ethanol as solvent,the reaction for48h at0℃. Substrate2-nitrobenzaldehyde obtained the ee value of86%, the substrate3-nitrobenzaldehyde get the best value of98%ee. However, underthis condition, only the nitro-substituted benzaldehydes of the substrate may obtaingood results, the effect of other aldehydes not ideal substrates. L15to this reaction,also failed to achieve good results.
Keywords/Search Tags:Chiral Schiff base N,O-ligand, Henry Asymmetric reactions, Nitromethane
PDF Full Text Request
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