Highly enantioselective aza-Henry reaction promoted by amine-functionalized tridentate sulfinyl ligands

Diastereomerically pure tridentate heteroorganic ligands containing hydroxyl, sulfinyl, and amino moieties as nucleophilic centers, capable of binding various organometallic reagents, have proven to be highly efficient catalysts in enantioselective aza-Henry reactions to give the desired products in very high yields (up to 98%) and with ees of up to 95%. The influence of the stereogenic centers, located on the sulfinyl sulfur atom and in the amino moiety on the stereochemical course of the reaction is also discussed. (C) 2011 Elsevier Ltd. All rights reserved.