Doubly Activated Cyclopropanes as Synthetic Precursors for the Preparation of 4-Nitro- and 4-Cyano-dihydropyrroles and Pyrroles
Organic Letters2005Vol. 7(12), pp. 2313–2316
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Abstract
[reaction: see text] 1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in situ-generated phenyliodonium ylides catalyzed by Rh(II) carboxylates. The doubly activated cyclopropanes were used as synthetic precursors for the regiospecific synthesis of 4-nitro- and 4-cyano-dihydropyrroles upon treatment with primary amines. Oxidation of the dihydropyrroles with DDQ allows rapid access to densely functionalized pyrroles.
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