| Autor: |
Badham NF; GlaxoSmithKline Pharmaceuticals, 709 Swedeland Road, King of Prussia, Pennsylvania 19406, USA. neil_f_badham@gsk.com, Mendelson WL, Allen A, Diederich AM, Eggleston DS, Filan JJ, Freyer AJ, Killmer LB Jr, Kowalski CJ, Liu L, Novack VJ, Vogt FG, Webb KS, Yang J |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2002 Jul 26; Vol. 67 (15), pp. 5440-3. |
| DOI: |
10.1021/jo025737g |
| Abstrakt: |
A convenient two-step homologation of both aliphatic and aromatic ketones to the corresponding carboxylic acid has been developed. First ketones were converted to epoxynitriles with the Darzens reaction. Second, a Lewis acid mediated rearrangement of these epoxynitriles with lithium bromide was achieved to give homologated secondary alkanoic acids (as well as aryl-alkanoic) in good yields. The mechanism and the scope of the rearrangement reaction were investigated. This strategy constitutes a two-step homologation of ketones to secondary carboxylic acids. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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