Enantioselective friedel-crafts alkylations with benzoylhydrazones promoted by a simple strained silacycle reagent |
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| Authors: | Shirakawa Seiji Berger Richard Leighton James L |
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| Institution: | Department of Chemistry, Columbia University, New York, New York 10027, USA. |
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| 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. |
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