title: Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions.
abstract: The regio- and enantioselective cyclization of pyrroles onto N-acyliminium ions generated in situ from hydroxylactams is reported. Modest to excellent ee's and yields are obtained in these novel Pictet-Spengler-type reactions with a chiral thiourea-pyrrole catalyst. Useful synthetic transformations of the versatile pyrroloindolizidinone and pyrroloquinolizidinone products are presented.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
authors.forename: Izzat T
authors.initials: IT
authors.lastname: Raheem
authors.forename: Parvinder S
authors.initials: PS
authors.lastname: Thiara
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines