title: C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.
abstract: A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C(2)-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted piperidines with excellent diastereoselectivity and enantiospecificity.
authors: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
authors: Feng
authors: F
authors: Chen
authors: Chong Kiat
authors: CK
authors: Tan
authors: Ying-Yeung
authors: YY
authors: Yeung
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D016566:Organoselenium Compounds; D010797:Phthalimides; C056577:N-bromophthalimide