Highly enantioselective Pictet-Spengler reactions with alpha-ketoamide-derived ketimines: access to an unusual class of quaternary alpha-amino amides.
"Quat's" the story? N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet-Spengler reaction of ketimines derived from alpha-ketoamides leading to quaternary alpha-amino acid derivatives (see scheme).
Bou-Hamdan
Farhan R
FR
Department of Chemistry, Columbia University, New York, NY 10027, USA.
Leighton
James L
JL
D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D006571:Heterocyclic Compounds; D012821:Silanes