Carbon−Carbon Bond Formation and Pyrrole Synthesis via the [3,3] Sigmatropic Rearrangement of O-Vinyl Oxime Ethers
Organic Letters2010Vol. 12(10), pp. 2290–2293
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Abstract
A new method for the synthesis of 2,4- and 2,3,4-substituted pyrroles in two or three steps from commercially available ketones and allyl hydroxylamine is described. An iridium-catalyzed isomerization reaction has been developed to convert O-allyl oximes to O-vinyl oximes, which undergo a facile [3,3] rearrangement to form 1,4-imino aldehyde Paal-Knorr intermediates that cyclize to afford the corresponding pyrroles. Optimization and examples of the isomerization and pyrrole formation are discussed.
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