Carbon-carbon bond formation and pyrrole synthesis via the [3,3] sigmatropic rearrangement of O-vinyl oxime ethers.

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.

DOI: 10.1021/ol100659q

Cite this paper

@article{Wang2010CarboncarbonBF, title={Carbon-carbon bond formation and pyrrole synthesis via the [3,3] sigmatropic rearrangement of O-vinyl oxime ethers.}, author={Heng-Yen Wang and Daniel M{\"{u}ller and Rachna M Sachwani and Hannah N Londino and Laura L Anderson}, journal={Organic letters}, year={2010}, volume={12 10}, pages={2290-3} }