Enantioselective epoxide ring opening catalyzed by bis(tetrahydroisoquinoline) N,N′ -dioxides
Four bis(tetrahydroisoquinoline) N,N ′-dioxides were used as catalysts for the epoxide ring opening with tetrachlorosilane under various conditions. A strong solvent effect on asymmetric induction was observed for each of the used catalysts. The highest achieved asymmetric induction for the opening of meso -stilbene oxide was 69% ee. Regarding the cycloalkene oxides, 56% ee was obtained in the reaction with cyclooctene oxide.