An efficient synthesis of 3-alkyl-1,5,3-dioxazepanes and their use as electrophiles in double-Mannich reactions |
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Authors: | Kevin Sparrow David Barker Margaret A. Brimble |
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Affiliation: | School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland, New Zealand |
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Abstract: | An efficient synthesis of 3-alkyl 1,5,3-dioxazepanes was developed for subsequent use in double-Mannich reactions with a variety of carbon-based nucleophiles. It was found that addition of methyltrichlorosilane to the dioxazepane led to a long-lasting reactive species that reacted rapidly with acid-sensitive ketones and β-ketoesters to afford azabicyclo[3.3.1]nonanes in good yield. |
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