Facile Construction of Tetrahydropyrrolizines by Iron-Catalyzed Double Cyclization of Alkene-Tethered Oxime Esters with 1,2-Disubstituted Alkenes.

Org Lett

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering , Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510 , Japan.

Published: May 2018

AI Article Synopsis

  • The iron-catalyzed cycloaddition reaction successfully transforms alkene-tethered oxime esters and 1,2-disubstituted alkenes into tetrahydropyrrolizines, which are often found in bicyclic alkaloids.
  • The process involves a two-step cyclization, starting with an intramolecular cyclization followed by an intermolecular one.
  • The generation of an imine moiety is crucial for ensuring regioselectivity in the reaction.

Article Abstract

The iron-catalyzed cycloaddition reaction of alkene-tethered oxime esters with 1,2-disubstituted alkenes afforded tetrahydropyrrolizines, the structural motif often seen in bicyclic alkaloids. The reaction proceeds through consecutive cycloaddition reactions. These include, first, intramolecular cyclization, followed by intermolecular cyclization with a 1,2-disubstituted alkene in a regioselective manner where an imine moiety first generated plays a pivotal role.

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http://dx.doi.org/10.1021/acs.orglett.8b01073DOI Listing

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