Synthesis of spirocarbamate oxindoles via intramolecular trapping of a β-silyl carbocation by an N-Boc group.

Benjamin H Shupe, Emily E Allen, Jacob P MacDonald, Sean O Wilson, Annaliese K Franz

Organic letters 2013 Jul 05

filter terms:

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 05;15(13):3218-21