title: Enantioselective friedel-crafts alkylations with benzoylhydrazones promoted by a simple strained silacycle reagent.
abstract: The enantioselective Friedel-Crafts reaction of electron-rich arenes and heteroarenes with the benzoylhydrazone of isopropyl glyoxylate mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the recovery of the pseudoephedrine in 99% yield was achieved. A simple model is advanced to explain the observed enantioselectivity.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: Seiji
authors.initials: S
authors.lastname: Shirakawa
authors.forename: Richard
authors.initials: R
authors.lastname: Berger
authors.forename: James L
authors.initials: JL
authors.lastname: Leighton