title: Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles.
abstract: The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.
authors.affiliation: Institut of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen (Germany).
authors.forename: Sadiya
authors.initials: S
authors.lastname: Raja
authors.forename: Masaki
authors.initials: M
authors.lastname: Nakajima
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
mesh_terms: D002384:Catalysis; D003500:Cyclization; D055664:Electrochemical Techniques; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds
keywords: Lewis acid catalysis; Nazarov reaction; electrocyclization; indole alkaloids