Chiral Brønsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1‑Hydrosilatrane

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...

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Published inJournal of organic chemistry Vol. 84; no. 9; pp. 5021 - 5026
Main Authors Skrypai, Vladislav, Varjosaari, Sami E, Azam, Fawwaz, Gilbert, Thomas M, Adler, Marc J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SILICON-COMPOUNDS
PHOSPHORUS
REAGENTS
ENANTIOSELECTIVE SYNTHESIS
COMPLEXES
REACTIVITY
TRANSFER HYDROGENATION
ALIPHATIC-KETONES
PENTACOORDINATE
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03073