Categories: O-H Bond Formation, C-H Bond Formation >
Reduction of epoxides
Recent Literature
Highly regioselective ring opening of epoxides with poor nucleophiles such as
indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and
sterically hindered tert-butylamine is a fast and convenient reaction in
the presence of 5.0 M lithium perchlorate-Et2O solution (LPDE).
A. Heydari, M. Mehrdad, A. Maleki, N. Ahmadi, Synthesis, 2004,
1557-1558.
The hydrogenation of α,β-epoxy ketones can be mediated by a catalytic amount
of BNA+Br- using Na2S2O4
as primary reducing agent to form the corresponding β-hydroxy ketones in
high yield. A radical mechanism has been proposed.
H.-J. Xu, Y.-C. Liu, Y. Fu, Y.-D. Wu, Org. Lett.,
2006, 8, 3449-3451.
The catalytic generation of activated carboxylates from epoxyaldehydes
enables a direct, anti-selective, convenient and mild synthesis of
β-hydroxyesters.
K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc.,
2004, 126, 8126-8127.
