title: Asymmetric allylic alkylation in combination with ring-closing metathesis for the preparation of chiral N-heterocycles.
abstract: Asymmetric copper-catalyzed allylic substitution with methylmagnesium bromide is employed in combination with ring-closing olefin metathesis or ene-yne metathesis to achieve the synthesis of chiral, unsaturated nitrogen heterocycles. The resulting six- to eight-membered chiral heterocycles are accessible in high yields and with excellent enantioselectivities.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors.forename: Johannes F
authors.initials: JF
authors.lastname: Teichert
authors.forename: Suyan
authors.initials: S
authors.lastname: Zhang
authors.forename: Anthoni W
authors.initials: AW
authors.lastname: van Zijl
authors.forename: Jan Willem
authors.initials: JW
authors.lastname: Slaa
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D006571:Heterocyclic Compounds