title: Enantioselective bromocyclization of allylic amides catalyzed by BINAP derivatives.
abstract: A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Kawato
authors.forename: Akino
authors.initials: A
authors.lastname: Kubota
authors.forename: Hiromi
authors.initials: H
authors.lastname: Ono
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Egami
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; C406943:BINAP, 2-naphthol; D009281:Naphthalenes; D001974:Bromosuccinimide