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...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
March 9, 2011
|
| In: |
Journal of the American Chemical Society
Year: 2011, Volume: 133, Issue: 13, Pages: 4774-4777 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja201008e |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja201008e
|
| Author Notes: | Stephanie Seel, Tobias Thaler, Keishi Takatsu, Cong Zhang, Hendrik Zipse, Bernd F. Straub, Peter Mayer, and Paul Knochel |
| Summary: | 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. |
|---|---|
| Item Description: | Gesehen am 31.10.2022 |
| Physical Description: | Online Resource |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja201008e |