Dual-activation asymmetric strecker reaction of aldimines and ketimines catalyzed by a tethered bis(8-quinolinolato) aluminum complex.J Am Chem Soc. 2009 Oct 28; 131(42):15118-9.JA
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.