Highly enantioselective catalytic acyl-pictet-spengler reactions.
The enantioselective cyclization of N-acyliminium ions generated in situ from tryptamine is promoted with high enantioselectivity by a new chiral thiourea catalyst. This represents the first successful system for asymmetric catalysis of the Pictet-Spengler reaction.
Taylor
Mark S
MS
Harvard University, Department of Chemistry and Chemical Biology, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Jacobsen
Eric N
EN
D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D007097:Imines / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives* / Q000737:chemistry
D002243:Carbolines; D007097:Imines; D026121:Indole Alkaloids; D013890:Thiourea