Tetrahedron Letters

Phase-transfer catalyzed asymmetric arylacetate alkylation

MB Andrus, KC Harper, MA Christiansen, MA Binkley

Index: Andrus, Merritt B.; Harper, Kaid C.; Christiansen, Michael A.; Binkley, Meisha A. Tetrahedron Letters, 2009 , vol. 50, # 31 p. 4541 - 4544

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Citation Number: 15

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 ...