Synthesis 2015; 47(15): 2188-2198
DOI: 10.1055/s-0034-1380229
special topic
© Georg Thieme Verlag Stuttgart · New York

Michael Addition Initiated Substrate- or Catalyst-Controlled Chemodivergent Three-Component Construction of Fused and Bridged Polycyclic Heterocycles

Haiying Du
Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France   Email: xavier.bugaut@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
,
Jean Rodriguez
Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France   Email: xavier.bugaut@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
,
Xavier Bugaut*
Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France   Email: xavier.bugaut@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
,
Thierry Constantieux*
Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France   Email: xavier.bugaut@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
› Author Affiliations
Further Information

Publication History

Received: 30 October 2014

Accepted after revision: 23 January 2015

Publication Date:
11 March 2015 (online)

Abstract

The results on the multicomponent reaction between cyclic β-keto esters, enals, and simple primary aliphatic amines are reported. In thermal conditions in the presence of 4 Å molecular sieves, two different­ families of heterocyclic products (aminobicyclo[3.3.1]nonanones or cycloalka[b]piperidines) were obtained depending on the presence of a substituent in the α-position of the aldehyde. Moreover, preliminary results on the possibility to obtain these two bicyclic cores from the very same starting materials by introducing organocatalysts with different activation modes in the reaction are presented.

Supporting Information

 
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