Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes: formal synthesis of (+/-)-erythro Juvabione.
[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.
Pearson
Anthony J
AJ
Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106, USA. anthony.pearson@case.edu
Paramahamsan
Harinandini
H
Dudones
James D
JD
D002857:Chromium / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D006492:Hempa; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D003510:Cyclohexanes; D009942:Organometallic Compounds; C414814:juvabione; C089514:tricarbonyl(eta(6)-2-trimethylsilylbenzaldehyde)chromium(0) complex; D002857:Chromium; D006492:Hempa