Skrypai Vladislav, Varjosaari Sami E, Azam Fawwaz, Gilbert Thomas M, Adler Marc J
Department of Chemistry & Biochemistry , Northern Illinois University , 1425 W. Lincoln Hwy. , DeKalb , Illinois 60115 , United States.
Department of Science & Mathematics , Coker College , 300 E. College Ave. , Hartsville , South Carolina 29550 , United States.
J Org Chem. 2019 May 3;84(9):5021-5026. doi: 10.1021/acs.joc.8b03073. Epub 2019 Apr 22.
The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Brønsted acid catalyst is reported. This is the first known example of chiral Brønsted acid-catalyzed asymmetric reductive amination using a silane as the hydride source. The reaction features a highly practical reducing reagent and proceeds efficiently at room temperature without a specialized reaction setup or equipment to exclude air or moisture. This method provides high conversion and enantiomeric excess up to 84% of the desired chiral secondary amines with minimal side products.
报道了使用1-氢硅氮烷与手性布朗斯特酸催化剂对手性酮与芳基胺进行不对称直接还原胺化反应。这是已知首例使用硅烷作为氢化物源的手性布朗斯特酸催化不对称还原胺化反应。该反应具有一种高度实用的还原剂，并且在室温下无需专门的反应装置或设备来排除空气或水分即可高效进行。该方法能实现高转化率，生成对映体过量高达84%的所需手性仲胺，且副产物极少。
