Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes.
[reaction: see text] A set of chiral aliphatic amino diselenides have been synthesized from readily available starting materials in a straightforward synthetic route via the ring-opening reaction of the parent aziridines. These ligands have been tested as catalysts for the enantioselective addition of diethylzinc to aldehydes. The influence of the alkyl group substituents on the stereoselectivity has been studied, and in the best case, an enantiomeric excess up to 99% could be obtained by using only 0.5 mol % of the chiral diselenide 3a.
Braga
Antonio L
AL
Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil. albraga@quimica.ufsm.br
Paixão
Marcio W
MW
Lüdtke
Diogo S
DS
Silveira
Claudio C
CC
Rodrigues
Oscar E D
OE
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; C454811:diethylzinc