Multicomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar cycloaddition of proline esters?

Chemical Communications Pub Date: 2013-10-09 DOI: 10.1039/C3CC47184E

Abstract

The synthesis of unnatural pyrrolizidines has been studied using a multicomponent-domino process involving proline or 4-hydroxyproline esters, an aldehyde and a dipolarophile. The formation of the iminium salt promotes the 1,3-dipolar cycloaddition affording highly substituted pyrrolizidines under mild conditions and high regio- and diastereoselectivities.

Graphical abstract: Multicomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar cycloaddition of proline esters
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