Reactions of alkyl azides and ketones as mediated by Lewis acids: Schmidt and Mannich reactions using azide precursors

…, K Schildknegt, KA Agrios, C Mossman…

Index: Desai, Pankaj; Schildknegt, Klaas; Agrios, Konstantinos A.; Mossman, Craig; Milligan, Gregory L.; Aube, Jeffrey Journal of the American Chemical Society, 2000 , vol. 122, # 30 p. 7226 - 7232

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Citation Number: 96

Abstract

The Lewis acid-promoted reactions of alkyl azides with ketones can afford several products. Chief among these result from a Schmidt-like insertion of the azide into the carbon-carbon bond adjacent to the carbonyl group. Alternatively, an acid-promoted rearrangement of the azide to an iminium species can occur, mostly with benzylic azides; the iminium species can then be trapped by the enol of the carbonyl compound in a variation of the Mannich ...