Microwave-assisted telescoped cross metathesis-ring closing aza-Michael reaction sequence: step-economical access to nicotine–lobeline hybrid analogues?

RSC Advances Pub Date: 2015-11-06 DOI: 10.1039/C5RA20930G

Abstract

A series of 2,5-disubstituted pyrrolidines was synthesized through an efficient telescoped cross-metathesis/cyclizing aza-Michael addition involving N-heteroaromatic olefinic derivatives. This synthetic route was applied to the preparation of original nicotine–lobeline, nicotine–pelletierine and lobeline–nicotine–epibatidine hybrids.

Graphical abstract: Microwave-assisted telescoped cross metathesis-ring closing aza-Michael reaction sequence: step-economical access to nicotine–lobeline hybrid analogues
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