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| LETTER | Synlett 2006: 3435-3438
DOI: 10.1055/s-2006-956473 |
© Georg Thieme Verlag Stuttgart · New York
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The Direct Introduction of Carbonates α to Carbonyl Groups
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| Adrian Halla, Kerri L. Jonesb, Teyrnon C. Jonesa, Niall M. Killeena, Robert Pörziga, Paul H. Taylora, Sze Chak Yaua, Nicholas C. O. Tomkinson*a |
a School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK
Fax: +44(29)20874030; e-Mail: tomkinsonnc@cardiff.ac.uk;
b Neurology & GI Centre of Excellence for Drug Discovery, GlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK
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Received
19 September 2006 |
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 prepared in two high-yielding steps from N-Boc-N-methyl hydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compounds to give the corresponding α-functionalised products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement. Key words
metal-free synthesis - hydroxylamine - carbonate
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