68641-85-0Relevant articles and documents
Enantioselective protonation of prochiral enolates in the asymmetric synthesis of (S)-naproxen
Mu?oz-Mu?iz, Omar,Juaristi, Eusebio
, p. 2023 - 2026 (2003)
Racemic methyl, iso-propyl, and tert-butyl ester derivatives of naproxen were treated with achiral LDA base to give the corresponding prochiral enolates 2-Li, 3-Li, and 4-Li. Protonation of these enolates with novel chiral proton sources (S)-10 and (S,S)-11, containing the α-phenylethylamino group, proceeded in a highly enantioselective manner. Saponification of enantioenriched ester derivatives 2-4 afforded naproxen, (S)-1, with no loss of enantiopurity.