Secondary amines as coupling partners in direct catalytic asymmetric reductive amination

Highly enantioselective hydrogen-transfer reductive amination: catalytic asymmetric synthesis of primary amines.

Optically active amines are attracting increasing interest in the food, agrochemical, and pharmaceutical industries as building blocks for novel compounds and as templates for asymmetric synthesis. One of the most common methods for preparing amines is the reductive amination of carbonyl compounds. We have successfully explored the rhodiumcatalyzed asymmetric reductive amination with hydrogen a...

Formal asymmetric biocatalytic reductive amination.

Stereoselective direct reductive amination of ketones with electron-deficient amines using Re2O7/NaPF6 catalyst.

The first example of direct reductive amination (DRA) of ketones with electron-deficient amines (EDA) such as Cbz-, Boc-, EtOCO-, Fmoc-, Bz-, ArSO2-, etc. protected amines have been achieved using catalytic Re2O7/NaPF6. Excellent chemoselectivities as well as diastereoselectivity (for 2-alkyl cyclohexanones) were obtained.

Catalytic Leuckart-Wallach-type reductive amination of ketones.

A CpRh(III) complex catalyzes reductive amination of ketones using HCOONH(4) at 50-70 degrees C to give the corresponding primary amines in high yields. The reaction is clean and operationally simple and proceeds at a lower temperature and with higher chemoselectivity than the original Leuckart-Wallach reaction. The new method has been applied to the synthesis of alpha-amino acids directly from...

Protecting-group-free synthesis of amines: synthesis of primary amines from aldehydes via reductive amination.

New methodology for the protecting-group-free synthesis of primary amines is presented. By optimizing the metal hydride/ammonia mediated reductive amination of aldehydes and hemiacetals, primary amines were selectively prepared with no or minimal formation of the usual secondary and tertiary amine byproduct. The methodology was performed on a range of functionalized aldehyde substrates, includi...