Asymmetric synthesis of ibuprofen via diastereoselective alkylation of a homochiral N-acylbornanesultam

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1539-1540

  Oppolzer, Wolfgang ^a   Rosset, Stephane ^a   De Brabander, Jef ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

IBUPROFEN;

ALKYLATION; ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550822     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00148-2     Document Type: Article

References (13)

1. 1) S. C. Stinson, Chem. Eng. News 1994, 72, 38.
2. 2) G. J. Lombardino, Non-steroidal Antiinflammatory Drugs, Wiley Interscience, New York, 1985.
3. 3) K. Brune, G. Geisslinger, S. Menzel-Soglovek, J. Clin. Pharmacol. 1992, 32, 944.
4. 4) For a review dealing with the asymmetric synthesis of α-arylpropanoic acids see: H. R. Sonawane, N. S. Bellur, J. R. Ahuja, D. G. Kulkarni, Tetrahedron: Asymmetry 1992, 3, 163.
5. 5) Asymmetric α-alkylation of carboxylic acids with low to modest selectivities have been reported: a) A. Ando, T. Shioiri, J. Chem. Soc., Chem. Commun. 1987, 656;
6. b) K. Fuji, M. Node, F. Tanaka, S. Hosoi, Tetrahedron Lett. 1989, 30, 2825.
7. 6) A. Fadel, Synlett 1992, 48.
8. 7) a) W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron. Lett. 1989, 30, 5603;
9. b) W. Oppolzer, I. Rodriguez, C. Starkemann, E. Walther, ibid. 1990, 31, 5019.
10. 8) S. D. Higgins, C. B. Thomas, J. Chem. Soc., Perkin Trans. 1 1982, 235.
11. 9) A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 18, 4171.
12. 13C NMR and mass spectra.
13. 11) Compound 1 was identified by comparison of the spectroscopic data with a commercial sample (Fluka AG, Switzerland). The enantiomeric excess was determined by chiral HPLC (chiralcel OD column, hexane/i-PrOH 100:1), comparatively to a racemic sample.