Effects of Magnesium Salts and Amines on the Stereoselectivity in the Imine Aldol Reaction

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  • ChemInform Abstract: Effects of Magnesium Salts and Amines on the Stereoselectivity in the Imine Aldol Reaction.

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In the imine aldol reactions of 1 with aromatic aldehydes using magnesium salts in the presence of amines, the threo/erythro ratios of products increased in the order Mg(ClO4)2>MgI2>MgBr2>MgCl2>Mg(OTf)2 and N,N,N′,N′-tetramethylethylenediamine (TMEDA)>Et3N. This increase in the threo/erythro ratios of products was estimated to be caused by a retro-imine aldol reaction under thermodynamic control.

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