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Stereoelectronic Basis for the Kinetic Resolution of N‐Heterocycles with Chiral Acylating Reagents |
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| Authors: | Sheng‐Ying Hsieh Benedikt Wanner Dr. Philip Wheeler Prof. Dr. André M. Beauchemin Prof. Dr. Tomislav Rovis Prof. Dr. Jeffrey W. Bode |
| Affiliation: | 1. Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir‐Prelog‐Weg 1–5, 8093 Zürich (Switzerland), Fax: (+41)?44‐633‐1235;2. Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523 (USA);3. Department of Chemistry, University of Ottawa, Ottawa, Ontario K1N 6N5 (Canada) |
| Abstract: | The kinetic resolution of N‐heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N‐heterocycles by using easily prepared reagents. A transition‐state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed. |
| Keywords: | hydroxamic acid kinetic resolution N‐heterocycles stereoelectronic effects synthetic methods |