A Two-Step Asymmetric Synthesis of (R)-Monoaryl Epoxides Using a Chiral Oxathiane as a Recoverable Reagent: Application to the Preparation of (R)-β-Adrenergic Compounds

Journal of Organic Chemistry

Volumn 60, Issue 11, 1995, Pages 3494-3498

  Solladié Cavallo, Arlette ^a   Diep Vohuule, Anh ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BETA ADRENERGIC RECEPTOR STIMULATING AGENT; DICHLORISOPRENALINE; PRONETALOL;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029041453     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00116a041     Document Type: Article

References (20)

1. Solladie-Cavallo, A.; Adib, A. Tetrahedron 1992, 48, 2453.
2. Breau, L.; Durst, T. Tetrahedron: Asymmetry 1991, 2, 367.
3. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791.
4. Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628.
5. Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333.
6. Eliel, E. L.; Lynch, J. E.; Kume, F.; Frye, S. V. Organic Syntheses; Vedejs, E., Ed.; Wiley: New York, 1987; Vol. 65, p 215.
7. Vedejs, E.; Engler, D. A.; Mullens, M. J. J. Org. Chem. 1977, 42, 3109.
8. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 5298.
9. Solladie-Cavallo, A.; Adib, A.; Schmitt, M.; Fischer, J.; DeCian, A. Tetrahedron: Asymmetry 1992, 3, 1597.
10. Eliel, E. L.; Wilier, R. L. J. Am. Chem. Soc. 1977, 99, 1936.
11. Dongala, E. B.; Solladié-Cavallo, A.; Solladié, G. Tetrahedron Lett. 1972, 4233.
12. Solladié, G.; Demailly, G.; Greek, C. Tetrahedron Lett. 1985, 26, 435.
13. Reagents, Catalysts and building Blocks. Merck-Schuchardt.
14. Medicinal Chemistry, Nogrady, T., Ed.; Oxford University Press: 1985; p 157.
15. Almirante, L.; Murmann, W. J. Med. Chem. 1966, 9, 650.
16. Howe, R.; Crowther, A. F.; Stephenson, J. S.; Rao, B. S.; Smith, L. H. J. Med. Chem. 1968, 11, 1000.
17. Howe, R.; Rao, B. S. J. Med. Chem. 1968, 11, 1118.
18. Solladié-Cavallo, A.; Bencheqroun, M. J. Org. Chem. 1992, 57, 5831.
19. Howe, R.; Shanks, R. G. Nature 1966, 210, 1336.
20. Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.