The direct introduction of carbonates α to carbonyl groups

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Hall, Adrian and Jones, Kerri L. and Jones, Teyrnon C. and Killeen, Niall M. and Porzig, Robert and Taylor, Paul H. and Yau, Sze Chak and Tomkinson, Nicholas C. O. (2006) The direct introduction of carbonates α to carbonyl groups. Synlett (20). pp. 3435-3438. ISSN 0936-5214 (https://doi.org/10.1055/s-2006-956473)

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Abstract

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.

ORCID iDs

Hall, Adrian, Jones, Kerri L., Jones, Teyrnon C., Killeen, Niall M., Porzig, Robert, Taylor, Paul H., Yau, Sze Chak and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
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