Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 9, Pages 5021-5026Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03073
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Funding
- Northern Illinois University
- Ryerson University
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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.
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