Aldol condensation via germanium enolates. Stereoselection dictated by the co-presence of lithium halides
Abstract
Trimethylgermanium enolates, prepared in situ from lithium enolates and trimethylgermanium halides, underwent a rapid aldol condensation with benzaldehyde to give the erythro-aldol predominantly, while the same enolates produced the threo-aldol preferentially if the coexisting lithium halides were removed before condensation.