Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin
M. Arjun Reddy, K. Surendra, N. Bhanumathi and K. Rama Rao*
*Organic Chemistry Division 1, Indian Institute of Chemical Technology,
Hyderabad 500 007, India, Email: ramaraok
iict.ap.nic.in
M. Arjun Reddy, K. Surendra, N. Bhanumathi, K. Rama Rao, Tetrahedron, 2002, 58, 6003-6008.
DOI: 10.1016/S0040-4020(02)00614-2
Abstract
Highly regioselective ring opening of epoxides to halohydrins has been carried out in impressive yields with hydrogen and lithium halides in presence of β-cyclodextrin using water as solvent.
| Epoxide | Reagent | Product | Yield (%, isol.) |
 |
HCl HBr HI LiCl LiBr LiI |
 |
96 90 89 89 85 82 |
 |
HCl HBr HI LiCl LiBr LiI |
 |
88 90 84 78 84 75 |
see article for more examples
N. S. Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2004, 501-502.
Key Words
Epoxides, Bromohydrins, Chlorohydrins, Iodohydrins, Hydrogen Halides, Lithium Halides, Cyclodextrin, Supramolecular Catalysis
ID: J72-Y2002-050
