An efficient synthesis of 3-alkyl-1, 5, 3-dioxazepanes and their use as electrophiles in double-Mannich reactions

K Sparrow, D Barker, MA Brimble

Index: Sparrow, Kevin; Barker, David; Brimble, Margaret A. Tetrahedron, 2012 , vol. 68, # 4 p. 1017 - 1028

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Citation Number: 3

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.