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.
Andrus, Merritt B.,Harper, Kaid C.,Christiansen, Michael A.,Binkley, Meisha A.
supporting information; experimental part
p. 4541 - 4544
(2009/12/03)
Biorestrictors and antibiotics. XL: Syntheses of dehydroorchinol methyl ether and dehydroorchinol
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Mueller,Seres,Steiner,et al.
p. 790 - 795
(2007/10/10)
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