| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5273809 | Tetrahedron Letters | 2009 | 4 Pages |
Abstract
Phenethyl arylacetates are alkylated under phase-transfer conditions with cinchona catalysts with alkyl halides in high yield with excellent enantioselectivity (84-99% ee) following recrystallization. Cinchonidine (CD) derived catalyst gave the (R)-product and cinchonine (CN) catalyst produced the (S)-product. The phenethyl (PE) ester group is removed, using ammonium formate and catalytic Pd/C, to give alkylated carboxylic acid products in high selectivity. The utility of the approach is demonstrated by a direct synthesis of (S)-naproxenâ¢.
Graphical abstractPhenethyl arylacetates are alkylated under phase-transfer conditions with cinchona catalysts.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Merritt B. Andrus, Kaid C. Harper, Michael A. Christiansen, Meisha A. Binkley,