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

Chem Commun (Camb)

Université de Rennes 1, UMR 6226 CNRS, Institut des Sciences Chimiques de Rennes, Equipe PNSCM, UFR des Sciences Biologiques et Pharmaceutiques, 2 Avenue du Prof. Léon Bernard, 35043 Rennes Cedex, France.

Published: July 2014

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.

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Source
http://dx.doi.org/10.1039/c4cc02826kDOI Listing

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