The first method for the direct formation of α-oxycarbonates from both aldehydes and ketones is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement.
- carbonyl groups
- hydrochloride reagents
Hall, A., Jones, K. L., Jones, T. C., Killeen, N. M., Porzig, R., Taylor, P. H., ... Tomkinson, N. C. O. (2006). The direct introduction of carbonates α to carbonyl groups. Synlett, (20), 3435-3438. https://doi.org/10.1055/s-2006-956473