Stereoselective Methodology for 1-Aryl-1-alkyl Epoxides via Chromium Tricarbonyl Complexes

Synlett

Volumn 1997, Issue 1, 1997, Pages 66-68

  Davies, S G ^a   Loveridge, T ^a   Clough, J M ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0141818474     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-705     Document Type: Article

References (15)

1. Sharpless, K. B.; Woodward, S. S.; Finn, M. G. Pure Appl. Chem., 1983, 55, 1823 and refs therein.
2. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc., 1990, 112, 2801.
3. Davies, S. G.; Loveridge, T; Clough, J. M. submitted for publication.
4. Hexaconazole [2-(2,4-dichlorophenyl)-1-(1,2,4-triazol-1-yl) hexan-2-ol] is marketed by ZENECA Agrochemicals as "ANVIL" or "PLANETE" a highly active broad-spectrum agricultural fungicide.
5. All arene chromium tricarbonyl complexes are racemic unless indicated otherwise with the appropriate stereochemical descriptor. Only a single enantiomer is illustrated in all schemes for clarity and corresponds to that designated first in any stereochemical descriptor given.
6. Davies, S. G.; Loveridge, T.; Clough, J. M. J. Chem. Soc., Chem. Commun. 1995, 817; Davies, S. G.; Loveridge, T; Clough, J. M. submitted for publication.
7. Davies, S. G.; Loveridge, T.; Clough, J. M. J. Chem. Soc., Chem. Commun. 1995, 817; Davies, S. G.; Loveridge, T; Clough, J. M. submitted for publication.
8. Levine, S. G.; Gopalakrishnan, B. Tetrahedron Lett., 1982, 23, 1239.
9. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1962, 84, 867. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1962, 84, 3782. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1965, 87, 1353.
10. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1962, 84, 867. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1962, 84, 3782. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1965, 87, 1353.
11. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1962, 84, 867. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1962, 84, 3782. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc., 1965, 87, 1353.
12. +, 3%), 405 (39%), 285 (95%), 269 (100%). Fraction 3: 2 as a red solid (4mg, 9%).
13. Worthington, P. A. Pestic. Sci., 1991, 31, 457. Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem., 1995, 60, 3000.
14. Worthington, P. A. Pestic. Sci., 1991, 31, 457. Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem., 1995, 60, 3000.
15. +, 41%), 246 (35%), 193 (43%), 178 (100%).