Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex.
An aluminum complex was found to be high yielding and enantioselective for the addition of cyanide to aldimines and ketimines. Although catalytic asymmetric addition of cyanide to imines to generate alpha-amino-protected nitriles (the Strecker reaction) has been extensively studied in the past, alternative, easier-to-handle reagents for this process are required for modern organic synthesis. To date, there are a limited number of reports utilizing alternative sources of cyanide other than KCN/HCN or TMSCN for this important reaction. The present catalyst provides uniformly high enantioselectivity for aromatic, heteroaromatic, and aliphatic aldimines and ketimines using ethyl cyanoformate as the cyanide source.
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Joshua P
JP
Abell
Hisashi
H
Yamamoto
D002384:Catalysis; D003486:Cyanides / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003486:Cyanides; D007097:Imines; D009942:Organometallic Compounds; C546808:bis(8-quinolinolato) aluminum