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Paper | Special issue | Vol 82, No. 2, 2011, pp.1297-1316
Published online: 2nd August, 2010
DOI: 10.3987/COM-10-S(E)77
Synthesis of Highly Substituted Nitropyrrolidines, Nitropyrrolizines and Nitropyrroles via Multicomponent-Multistep Sequences within a Flow Reactor

Marcus Baumann, Ian R. Baxendale, Andreas Kirschning, Steven V. Ley,* and Jens Wegner

*Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge
CB2 1EW, U.K.

Abstract

We expand upon recent results concerning dipolar cycloaddition reactions of unstabilized azomethine ylids with nitro alkenes to generate 3-nitropyrrolidines via a flow chemistry sequence. This new work describes the development of a three-component coupling reaction between glycine esters, aldehydes and nitro alkenes. In order to further demonstrate the utility of flow technology in concert with heterogeneous reagents and scavengers for complex reaction sequences an in-line oxidation resulting in the conversion of tetra-substituted pyrrolidines to their pyrrole congeners has been developed.

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