Enantioselective synthesis of alpha-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst.
[formula: see text] A novel catalytic enantioselective Strecker synthesis of chiral alpha-amino nitriles and alpha-amino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity. Key features of the enantioselective process include (1) the use of the chiral bicyclic guanidine 1 as catalyst and (2) the use of the N-benzhydryl substituent on the imine substrate.
Corey
E J
EJ
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. corey@chemistry.harvard.edu
Grogan
M J
MJ
D001559:Benzhydryl Compounds / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D006146:Guanidines / Q000737:chemistry*; D006856:Hydrogen Cyanide / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis*; D008958:Models, Molecular; D009570:Nitriles / Q000138:chemical synthesis*; D012545:Schiff Bases; D013237:Stereoisomerism
D001559:Benzhydryl Compounds; D001643:Bridged Bicyclo Compounds; D006146:Guanidines; D007097:Imines; D009570:Nitriles; D012545:Schiff Bases; D006856:Hydrogen Cyanide