Highly diastereoselective arylations of substituted piperidines
A highly diastereoselective methodology for the preparation of various substituted piperidines via Negishi cross-couplings with (hetero)aryl iodides was developed. Depending on the position of the C−Zn bond relative to the nitrogen (position 2 vs position 4), the stereoselectivity of the coupling ca...
Gespeichert in:
| Hauptverfasser: | , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
March 9, 2011
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| In: |
Journal of the American Chemical Society
Year: 2011, Jahrgang: 133, Heft: 13, Pages: 4774-4777 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja201008e |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja201008e
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| Verfasserangaben: | Stephanie Seel, Tobias Thaler, Keishi Takatsu, Cong Zhang, Hendrik Zipse, Bernd F. Straub, Peter Mayer, and Paul Knochel |
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| 520 | |a A highly diastereoselective methodology for the preparation of various substituted piperidines via Negishi cross-couplings with (hetero)aryl iodides was developed. Depending on the position of the C−Zn bond relative to the nitrogen (position 2 vs position 4), the stereoselectivity of the coupling can be directed toward either the trans- or cis-2,4-disubstituted products. Density functional theory calculations on the relative stabilities of the Zn and Pd intermediates were performed to explain the high diastereoselectivities obtained. A novel 1,2-migration of Pd further expands this method to the stereoselective preparation of 5-aryl-2,5-disubstituted piperidines. | ||
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