| Autor: |
Wisniewska HM; Department of Chemistry, University of California, Irvine, California 92697-2025, USA., Swift EC, Jarvo ER |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2013 Jun 19; Vol. 135 (24), pp. 9083-90. Date of Electronic Publication: 2013 Jun 10. |
| DOI: |
10.1021/ja4034999 |
| Abstrakt: |
The first Negishi nickel-catalyzed stereospecific cross-coupling reaction of secondary benzylic esters is reported. A series of traceless directing groups is evaluated for ability to promote cross-coupling with dimethylzinc. Esters with a chelating thioether derived from commercially available 2-(methylthio)acetic acid are most effective. The products are formed in high yield and with excellent stereospecificity. A variety of functional groups are tolerated in the reaction including alkenes, alkynes, esters, amines, imides, and O-, S-, and N-heterocycles. The utility of this transformation is highlighted in the enantioselective synthesis of a retinoic acid receptor agonist and a fatty acid amide hydrolase inhibitor. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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