The direct formation of α-carbamates from carbonyl compounds

Hall, Adrian and Huguet, Edouard P. and Jones, Kerri L. and Jones, Teyrnon C. and Killeen, Niall M. and Yau, Sze Chak and Tomkinson, Nicholas C. O. (2007) The direct formation of α-carbamates from carbonyl compounds. Synlett (2). pp. 293-297. ISSN 0936-5214

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A simple one-pot method for the direct introduction of carbamates α to carbonyl groups that proceeds at room temp. in the presence of both moisture and air was developed. Treatment of aldehydes and both cyclic and acyclic ketones with N-methyl-O-carbamoyl hydroxylamine hydrochlorides provides the α-functionalized products in 50-88% isolated yield. The transformation is tolerant of a range of functional groups within the substrate and is also effective for the introduction of a variety of oxycarbamoyl groups.