Asymmetric radical cyclization reactions of axially chiral N-allyl-o-iodoanilides to form enantioenriched N-acyl dihydroindoles |
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Authors: | Dennis P Curran AndreJB Lapierre |
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Institution: | Department of Chemistry, University of Pittsburgh, Parkman Avenue, University Drive, Pittsburgh, PA 15260, USA |
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Abstract: | Radical cyclizations of enantiomerically enriched N-allyl-o-iodoanilides provide N-acyl-3-alkyl-2,3-dihydroindoles in good yields and with good to excellent levels of chirality transfer from the N-Ar axis to the new stereocenter. In competitive cyclizations of N-acryloyl-N-allyl-o-iodoanilides, the addition of an o-methyl group reverses the regioselectivity of the radical cyclization from the acryloyl group to the allyl group. Approximate rate constants for representative radical cyclizations have been measured to provide insight into the origin of these observations. |
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Keywords: | Axially chiral N-allyl-o-iodoanilides Intramolecular reaction Radical cyclization |
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