Phase-Transfer Catalyzed Asymmetric Arylacetate Alkylation

Document Type

Article

Journal/Book Title

Synfacts

Publication Date

2009

Publisher

Thieme Publishing

Volume

8

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)-naproxen™.

This document is currently not available here.

Share

COinS