Rapid assembly of anti-1,3-diol units with 2-quaternary carbon stereocenter via samarium diiodide-promoted tandem Aldol/Evans-Tishchenko reaction

An efficient and practical method for highly diastereoselective synthesis of 2-quaternary anti-1,3-diol units with three adjacent stereogenic carbon centers has been developed. The reactions proceed regiospecifically at room temperature via samarium diiodide-promoted tandem Aldol condensation and Evans-Tishchenko reduction. The relative stereochemistry of the resulting 1,3-diol monoesters is identified by X-ray crystallography.