Categories: C=O Bond Formation >
Synthesis of aldehydes
Reactions
Oxidation of alcohols, rearrangements
Recent Literature

o-Iodoxybenzoic acid (IBX) was found to be highly effective in oxidations
adjacent to carbonyl and benzylic functionalities to form either α,β-unsaturated carbonyl compounds
or conjugated aromatic carbonyl systems. Fine-tuning of the
reaction conditions allowed remarkably selective transformations within
multifunctional substrates.
K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc., 2002, 124, 2245-2258.

Chromium(III) tetraphenylporphyrin triflate is an efficient and
characteristic Lewis acid catalyst for a regio- and stereoselective
rearrangement of epoxides to aldehydes. Optically active β-siloxy aldehydes
are easily available through Sharpless epoxidation of allylic alcohols,
followed by silylation and rearrangement.
K. Suda, T. Kikkawa, S.-i. Nakajima, T. Takanami, J. Am. Chem. Soc.,
2004, 126, 9554-9555.
