title: Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes.
abstract: [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.
authors.affiliation: Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, 97105-900, Brazil. albraga@quimica.ufsm.br
authors.forename: Antonio L
authors.initials: AL
authors.lastname: Braga
authors.forename: Marcio W
authors.initials: MW
authors.lastname: Paixão
authors.forename: Diogo S
authors.initials: DS
authors.lastname: Lüdtke
authors.forename: Claudio C
authors.initials: CC
authors.lastname: Silveira
authors.forename: Oscar E D
authors.initials: OE
authors.lastname: Rodrigues
mesh_terms: 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
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; C454811:diethylzinc