Organocatalyst-promoted Diastereoselective and Enantioselective Michael Addition/Hemiketalization Reaction between Hydroxymaleimide and Quinone

An organocatalyst promoted diastereoselective and enantioselective Michael addition/hemiketalization reaction between hydroxymaleimides and quinones has been demonstrated. The catalytic protocol allows for the efficient and mild synthesis of a broad range of new and versatile dihydrobenzofurans containing chiral hemiketal and succinimide frameworks from readily available starting materials in moderate to excellent yields (up to 95%) with good to excellent enantioselectivities (up to 95 : 5 er) and diastereoselectivities (all with at least 99 : 1 dr).

Automated summary

The study demonstrates an organocatalyst promoted diastereoselective and enantioselective reaction, allowing for the efficient and mild synthesis of a broad range of new and versatile dihydrobenzofurans containing chiral hemiketal and succinimide frameworks. The reaction yields moderate to excellent results (up to 95%) with good to excellent enantioselectivities (up to 95 : 5 er) and diastereoselectivities (all with at least 99 : 1 dr).