Synthesis of Novel Amino‐Acid‐Derived Sulfinamides and Their Evaluation as Ligands for the Enantioselective Transfer Hydrogenation of Ketones

Abstract

AbstractNovel chiral mono‐sulfinyl diamines bearing a stereogenic sulfur atom were prepared in moderate to good yields starting from amino acids by means of a reductive amination of the corresponding amino aldehydes. Their potential as ligands for asymmetric catalysis was evaluated in the metal‐catalyzed enantioselective transfer hydrogenation of alkyl‐aryl ketones. The catalysts were generated in situ from sulfinamides 1a–i and arene complexes of rhodium and ruthenium, and the catalytic reductions led to the formation of chiral alcohols with up to 91 % ee. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)