Enantioselective Prins cyclization: BINOL-derived phosphoric acid and CuCl synergistic catalysis.

Claudia Lalli (1) , Pierre van de Weghe (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

The first catalytic enantioselective Prins cyclization is disclosed. The reaction is catalyzed by the combination of a chiral BINOL-derived bis-phosphoric acid and CuCl. The process consists of a tandem Prins/Friedel-Crafts cyclization that affords the hexahydro-1H-benzo[f]isochromenes products with three new contiguous stereogenic centers in high yields, and good enantio- and excellent diastereoselectivities.

Domaines: Chimie; Catalyse

Claudia Lalli, Pierre van de Weghe. Enantioselective Prins cyclization: BINOL-derived phosphoric acid and CuCl synergistic catalysis.. Chemical Communications, 2014, 50 (56), pp.7495-8. ⟨10.1039/C4CC02826K⟩. ⟨hal-01116325⟩