Journal
JOURNAL OF COMBINATORIAL CHEMISTRY
Volume 5, Issue 2, Pages 188-196Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cc020079z
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Funding
- NIGMS NIH HHS [GM-56154] Funding Source: Medline
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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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