The direct catalytic asymmetric alpha-aminomethylation of ketones

ORGN 758

Ismail Ibrahem, isse@organ.su.se, Jesus Casas, jesus.casas@organ.su.se, and Armando Córdova, acordova@organ.su.se. Department of Organic Chemistry, Stockholm University, Svante Arrhenius v. 12, Stockholm, SE 106 91, Sweden
The direct amino acid-catalyzed asymmetric syntheses of alpha-aminomethylated ketones are presented. The organocatalytic reactions between unmodified ketones, aqueous formaldehyde and anilines proceeded with excellent enantioselectivities. The classical Mannich reactions were catalyzed by proline and its derivatives. In most cases, the corresponding products were isolated in high yield and with >99% ee. Methyl alkyl ketones were regioselectively alpha-aminomethylated at the methylene carbon affording the corresponding ketones with up to >99% ee.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005