Chiral Bronsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane
Chiral Bronsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane
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DOI：
10.1021/acs.joc.8b03073
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发表时间：
2019-05-03
影响因子：
3.6
通讯作者：
Adler, Marc J.
中科院分区：
文献类型：
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作者：
Skrypai, Vladislav;Varjosaari, Sami E.;Adler, Marc J.
报道了1-氢硅烷手性Bronsted酸催化前手性酮与芳胺的不对称直接还原胺化反应。这是已知的第一个使用硅烷作为氢化物源的手性Bronsted酸催化不对称还原胺化反应的例子。该反应采用高度实用的还原剂，在室温下有效进行，无需专门的反应装置或设备来排除空气或水分。该方法提供高转化率和对映体过剩高达84%所需的手性仲胺和最小的副产物。
The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Bronsted acid catalyst is reported. This is the first known example of chiral Bronsted 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.