Catalytic asymmetric three-component acyl-Strecker reaction.
The first organocatalytic asymmetric three-component Strecker reaction, the urea-catalyzed acylcyanation of in situ generated imines, has been developed. Different alpha-amido nitriles are formed in excellent yields and enantioslectivities from aldehydes, amines, and acyl cyanides in the presence of Jacobsen's thiourea catalyst 5. Despite its obvious use for the synthesis of alpha-amino acids and their derivatives, our reaction may find use in diversity oriented synthesis and medicinal chemistry. [reaction: see text]
Pan
Subhas Chandra
SC
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
List
Benjamin
B
D000215:Acylation; D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000447:Aldehydes; D000577:Amides; D000588:Amines; D000596:Amino Acids; D003486:Cyanides; D007097:Imines; D009570:Nitriles; D013890:Thiourea