Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions.
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.
Raheem
Izzat T
IT
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
Thiara
Parvinder S
PS
Jacobsen
Eric N
EN
D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D013237:Stereoisomerism
D007097:Imines