Solid-phase rhodium carbenoid N-H insertion reactions: the synthesis of a diverse array of indoles |
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Authors: | Lee Sang-Hyeup Clapham Bruce Koch Guido Zimmermann Jürg Janda Kim D |
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Affiliation: | The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. |
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Abstract: | A solid-phase synthesis of an array of indoles is reported. The key step in our approach involves a N-H insertion reaction of N-alkylanilines into a highly reactive polymer-bound rhodium carbenoid intermediate to yield the corresponding alpha-arylamino-beta-ketoester. These insertion products were then treated under acid-catalyzed cyclodehydration conditions to yield a series of polymer-bound indole esters, which were subsequently cleaved from the resin under Lewis acid-promoted amidation conditions to yield the desired indoles in good yields and with excellent purities. |
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