Phase-Transfer Catalyzed Asymmetric Arylacetate Alkylation

Authors

Merritt B. Andrus, Brigham Young University
Kaid C. Harper, Brigham Young University
Michael A. Christiansen, Utah State UniversityFollow
Meisha A. Binkley, Brigham Young University

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™.

Recommended Citation

Andrus, M. B.; Harper, K. C.; Christiansen, M. A.; Binkley, M. A. “Phase-Transfer Catalyzed Asymmetric Arylacetate Alkylation.” Synfacts, 2009, 8, 920.