The anion prepared from N-Boc-3-(tosylmethyl)indole using NaH in DMF can be readily functionalized by reaction with various electrophiles. The obtained sulfonyl indoles, upon removal of the N-protecting group, undergo nucleophilic attack via a vinylogous imino derivative, leading to branched 3-substituted indoles.
Double functionalization of N-Boc-3-(tosylmethyl)indole exploiting the activating properties of the tosyl group
PALMIERI, Alessandro;PETRINI, Marino;SHAIKH, RAFIK RAJJAK
2008-01-01
Abstract
The anion prepared from N-Boc-3-(tosylmethyl)indole using NaH in DMF can be readily functionalized by reaction with various electrophiles. The obtained sulfonyl indoles, upon removal of the N-protecting group, undergo nucleophilic attack via a vinylogous imino derivative, leading to branched 3-substituted indoles.File in questo prodotto:
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