Lalli Claudia, van de Weghe Pierre
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.
Chem Commun (Camb). 2014 Jul 18;50(56):7495-8. doi: 10.1039/c4cc02826k.
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.
首次公开了催化对映选择性普林斯环化反应。该反应由手性联萘酚衍生的双磷酸与氯化铜组合催化。该过程包括串联普林斯/傅克环化反应,能以高产率得到具有三个相邻新立体中心的六氢-1H-苯并[f]异色烯产物,对映选择性良好,非对映选择性优异。