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Synfacts 2009(8): 0920-0920  
DOI: 10.1055/s-0029-1217584
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Phase-Transfer-Catalyzed Asymmetric α-Alkylation of Esters

Contributor(s): Benjamin List, Ilija Èorić
M. B. Andrus*, K. C. Harper, M. A. Christiansen, M. A. Binkley
Brigham Young University, Provo, USA
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

A catalytic asymmetric α-alkylation of phenethyl arylacetates 2 with alkyl halides was presented. Under phase-transfer conditions using cinchona alkaloid derived catalysts 1, products 4 were obtained in reasonable yields with good enantioselectivity after recrystallization. The phenethyl ester group could be easily removed, using ammonium formate and catalytic Pd/C, to give α-alkylated carboxylic acid products. An application of this method was demonstrated with a short synthesis of (S)-naproxen.