Enantioselective Synthesis of Naproxen

The optically active naproxen was synthesized in good chemical yield and high optical purity starting from a chiral α-ketoalcohol which was prepared from enzymatic resolution of the corresponding racemic acetate using lipase as a catalyst.

[1]  Asensio González.  ASYMMETRIC SYNTHESIS OF 2-ARYLPROPIONIC ACIDS , 1991 .

[2]  H. R. Sonawane,et al.  Stereospecific 1,2-aryl migration in 2-hydroxy alkyl aryl acetals with PPh3/CCl4. Syntheses of optically active ibuprofen and naproxen , 1991 .

[3]  K. Tamaki,et al.  Preparation of Methyl 2-Arylpropanoates by the Reaction of 2-Hydroxypropiophenone Dimethyl Acetals with Sulfuryl Chloride in the Presence of an Amide or a Weak Base , 1987 .

[4]  T. Hiyama,et al.  Substitution at Secondary Benzylic Carbon with Aluminum Reagents: A Facile Synthesis of (±)-Naproxen , 1986 .

[5]  J. Rieu,et al.  Tetrahedron report number 205 , 1986 .

[6]  Y. Hamada,et al.  New Methods and Reagents in Organic Synthesis. 35. A New Synthesis of Some Non-Steroidal Anti-Inflammatory Agents with the 2-Arylpropionic Acid Skeleton by the Use of Diphenyl Phosphorazidate (DPPA) as a 1, 3-Dipole , 1983 .

[7]  G. Tsuchihashi.  Synthesis of optically active 2-arylalkanoic acids by the use of 1,2-rearrangement of the aryl group , 1983 .

[8]  C. Giordano,et al.  Esters of α-arylalkanoic acids from ‘masked’α-halogenoalkyl aryl ketones and silver salts: synthetic, kinetic, and mechanistic aspects , 1982 .

[9]  S. Mitamura,et al.  A new method for the synthesis of α-arylalkanoic acids by the use of 1,2-rearrangement of the aryl group☆ , 1981 .

[10]  I. Harrison,et al.  Nonsteroidal antiinflammatory agents. I. 6-substituted 2-naphthylacetic acids. , 1970, Journal of medicinal chemistry.