Enantioselective Synthesis of Benzodihydrofurans Bearing Axial and Central Stereogenic Elements

The enantioselective synthesis of chiral compounds containing multiple stereogenic elements via a single catalytic step is a challenging process. In the presence of α-chloronitrostyrenes and a chiral squaramide catalyst, C-C or C-N pro-axially chiral 2-naphthol substrates, featuring low barriers to enantiomerization, underwent a remote diastereo- and enantioselective domino Michael/O-alkylation. It provided the desired benzodihydrofurans bearing two stereogenic carbon atoms and a configurationally stable C-C or a C-N bond, thanks to a high increase of the barrier to rotation upon dihydrofurannulation.