title: Thiourea-catalyzed enantioselective iso-Pictet-Spengler reactions.
abstract: A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-γ-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-protected products by trituration or crystallization provides the optically pure tetrahydro-γ-carboline derivatives in a scalable and highly practical procedure.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
authors.forename: Yunmi
authors.initials: Y
authors.lastname: Lee
authors.forename: Rebekka S
authors.initials: RS
authors.lastname: Klausen
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D002243:Carbolines; D014363:Tryptamines; C055572:gamma-carboline; D019817:Benzoic Acid; D013890:Thiourea