Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts.
The formation and 2-amino alcohol catalyzed addition of arylzinc reagents from and with boronic acids, respectively, is drastically accelerated to a few minutes under microwave irradiation without loss of enantioselectivity (up to 98% ee). Of the amino acid derived catalysts tested, the conformationally restricted bulky substituted aziridine-2-methanols derived from serine show the best overall performance in the formation of diarylmethanols.
Braga
Antonio L
AL
Universidade Federal de Santa Maria, Departamento de Química, 97105-900, Santa Maria RS, Brazil. albraga@quimica.ufsm.br
Paixão
Marcio W
MW
Westermann
Bernhard
B
Schneider
Paulo H
PH
Wessjohann
Ludger A
LA
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D000447:Aldehydes / Q000737:chemistry* / Q000528:radiation effects; D001388:Aziridines / Q000737:chemistry* / Q000528:radiation effects; D001897:Boronic Acids / Q000737:chemistry / Q000528:radiation effects; D002384:Catalysis; D008024:Ligands; D008872:Microwaves; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry* / Q000528:radiation effects
D000438:Alcohols; D000447:Aldehydes; D001388:Aziridines; D001897:Boronic Acids; D008024:Ligands; D009942:Organometallic Compounds; D015032:Zinc