title: Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes: formal synthesis of (+/-)-erythro Juvabione.
abstract: [reaction: see text] Vicinal stereocontrol during nucleophilic addition of tert-butyl lithiopropionate to eta(6)-anisole chromium tricarbonyl complexes with differing para substituents has been studied. Excellent vicinal double stereoinduction (>99:1) was observed when the para substituent was Si(CH(3))(3), and this has been applied to a stereoselective formal synthesis of (+/-)-erythro Juvabione. Asymmetric synthesis by chiral auxiliary directed nucleophilic addition is also discussed.
authors.affiliation: Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106, USA. anthony.pearson@case.edu
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Pearson
authors.forename: Harinandini
authors.initials: H
authors.lastname: Paramahamsan
authors.forename: James D
authors.initials: JD
authors.lastname: Dudones
mesh_terms: D002857:Chromium / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D006492:Hempa; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003510:Cyclohexanes; D009942:Organometallic Compounds; C414814:juvabione; C089514:tricarbonyl(eta(6)-2-trimethylsilylbenzaldehyde)chromium(0) complex; D002857:Chromium; D006492:Hempa