Enantioselective Synthesis of Benzodihydrofurans Bearing Axial and Central Stereogenic Elements

Abstract

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.