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The study on the application of a new class of chiral 1,4-dimine catalysts to the catalytic asymmetric Henry reaction in water

Miao-Xi Liu  Peng Liu  
【摘要】:Chiral diamine ligand is one of the most important ligands in asymmetric catalytic reaction.Among them,the majority is about 1,2-diamine[1]and about 1,4-diamine[2]is rarely seen reports.Enantioselective Henry reactions have been extensively studied since 1992[3],However,there is a relatively small number of successful studies for the asymmetric Henry reactions in water[4].We have develop a new class of chiral 1,4-dimine thiourea catalysts bearing two 1,4-dioxane and a structure of cinchona alkaloids and it was applied in catalytic asymmetric Henry.After a preliminary screening conditions,we get good yields and up to 78%ee of 5mol%catalyst at low temperature(-30℃)in toluene.To our delighted,the reaction system is no-sensitive to moisture,it also obtain good yields and enantioselectivities(up to 75%ee)in toluene/H2O as a co-solvents or in the saturated brine,especially in water,it can also works well.Further investigation of the new catalyst is ongoing in our laboratory.

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