Synthesis of Novel Amino-Acid-Derived Sulfinamides and Their Evaluation as Ligands for the Enantioselective Transfer Hydrogenation of Ketones
作者:Lorenzo Zani、Lars Eriksson、Hans Adolfsson
DOI:10.1002/ejoc.200800576
日期:2008.9
Novel 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
通过相应氨基醛的还原胺化从氨基酸开始,以中等至良好的产率制备了带有立体异构硫原子的新型手性单亚磺酰基二胺。在金属催化的烷基芳基酮的对映选择性转移氢化中评估了它们作为不对称催化配体的潜力。催化剂是由亚磺酰胺 1a-i 和铑和钌的芳烃配合物原位生成的,催化还原导致形成手性醇,其 ee 含量高达 91%。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)