Copper-catalyzed electrophilic amination of a triarylboroxin using an N-methoxyamine to give quick access to a variety of anilines was reported. The reaction was especially useful for syntheses of functionalized anilines when combined with our previously reported nucleophilic addition to N-methoxyamides.
The synthesis of (±)-lasubine II has been achieved through a three-component allylation capitalizing on the unique properties of N-methoxyamines. This reaction enabled the installation of all the carbon atoms of lasubine II in a single operation. The N-methoxy group was efficiently used for the subsequent nitrone formation. A single-step cyclization of isoxazolidines or N-methoxyamines to form functionalized piperidine rings was also developed.
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