title: FeCl3-catalyzed cyclization of α-sulfonamido-allenes with aldehydes--the substituent effect.
abstract: FeCl(3)-catalyzed aza-Prins-cyclization reaction of α-sulfonamido-allenes with aldehydes afforded 1,2,3,6-tetrahydropyridine or 2,5-dihydro-1H-pyrrole derivatives efficiently and highly selectively. The different regioselectivity is probably caused by the stabilizing effect of the phenyl group on the positively charged allylic intermediate.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
authors.forename: Jiajia
authors.initials: J
authors.lastname: Cheng
authors.forename: Xinjun
authors.initials: X
authors.lastname: Tang
authors.forename: Yihua
authors.initials: Y
authors.lastname: Yu
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D002712:Chlorides; D005290:Ferric Compounds; D011725:Pyridines; D011758:Pyrroles; D013449:Sulfonamides; C025947:propadiene; C023666:pyridine; C024555:ferric chloride