Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 15, 2018
Previous Article Next Article

The dual reactivity of Weinreb amides applied to the late-stage divergent functionalisation of meso pyrrolidines

Author affiliations

Abstract

By exploiting the dual reactivity of a Weinreb amide moiety, i.e. nucleophilic addition or N–O reductive cleavage, a series of diversified symmetrical and dissymmetrical pyrrolidine analogues of lobelanine were synthesized from simple and readily available building blocks. Diversity is introduced at a late stage by using a wide variety of readily available organolithium and organomagnesium reagents, and chemoselective orientation can be achieved due to the steric encumbrance of both the reaction partners, the liganding ability of the starting meso pyrrolidine, and the nature of the organometallic species. This work constitutes the first example that takes advantage of the side reaction of Weinreb amide decomposition for the desymmetrization of a meso platform bearing two remote and highly flexible N-methoxy-N-methylamide arms through a probable beneficial metal-templated arrangement.

Graphical abstract: The dual reactivity of Weinreb amides applied to the late-stage divergent functionalisation of meso pyrrolidines

Back to tab navigation

Supplementary files

Article information


Submitted
23 Apr 2018
Accepted
29 May 2018
First published
30 May 2018

New J. Chem., 2018,42, 12403-12411
Article type
Paper

The dual reactivity of Weinreb amides applied to the late-stage divergent functionalisation of meso pyrrolidines

H. Boufroura, L. Sevaille, N. Gigant, E. Drège and D. Joseph, New J. Chem., 2018, 42, 12403
DOI: 10.1039/C8NJ01975D

Social activity

Search articles by author

Spotlight

Advertisements