Tetrahedron

Intramolecular Schmidt reactions of alkyl azides with ketals and enol ethers

CJ Mossman, J Aubé

Index: Mossman, Craig J.; Aube, Jeffrey Tetrahedron, 1996 , vol. 52, # 10 p. 3403 - 3408

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Citation Number: 27

Abstract

The ketals or enol ethers of 1, 5-azidoketones were converted into lactams using a two- stage process. Treatment of the ketals and enol ethers with acid (trifluoroacetic acid, triflic acid, or trimethylsilyl triflate) afforded an oxonium ion which reacted with the tethered azide to give a 1, 1-azido-alkoxy intermediate. Bond reorganization led to an iminium ether that was reacted with sodium iodide in acetone to expose the amide products. Seven ...