title: Stereoselectivity of the benzannulation reaction: efficient central-to-axial chirality transfer.
abstract: High diastereoselectivity is observed in the preparation of configurationally stable allocolchicinoids 5 from Fischer carbene complexes 4 and 1-pentyne. The analogous reaction of complexes 8 gives 9 with moderate diastereoselectivity for the opposite atropisomer and this selectivity can be taken to high levels under thermodynamic conditions.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Vorogushin
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
authors.forename: Hans-Jürgen
authors.initials: HJ
authors.lastname: Hansen
mesh_terms: D003078:Colchicine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C032782:allocolchicine; D003078:Colchicine