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We report the Lewis acid catalyzed additions of allylsilanes to N-Boc-iminooxindoles and the formation of novel silicon-containing spirocarbamates via intramolecular trapping of a β-silyl carbocation by an N-Boc group. Several transformations display the synthetic utility of these spirocarbamate oxindoles, including a reductive cyclization to access new silylated furoindoline derivatives.

Citation

Benjamin H Shupe, Emily E Allen, Jacob P MacDonald, Sean O Wilson, Annaliese K Franz. Synthesis of spirocarbamate oxindoles via intramolecular trapping of a β-silyl carbocation by an N-Boc group. Organic letters. 2013 Jul 5;15(13):3218-21

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PMID: 23758331

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