Vicinal Stereocontrol during Nucleophilic Addition to Arene Chromium Tricarbonyl Complexes: Formal Synthesis of (±)-erythro Juvabione

摘要

Vicinal stereocontrol during nucleophilic addition of tert-butyl lithiopropionate to η~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.