Synthesis 2013; 45(12): 1659-1666
DOI: 10.1055/s-0033-1338844
special topic
© Georg Thieme Verlag Stuttgart · New York

Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Functionalized Cyclohexanes

Wilfried Raimondi
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
,
Maria del Mar Sanchez Duque
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
,
Sébastien Goudedranche
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
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Adrien Quintard
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
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Thierry Constantieux
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
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Xavier Bugaut*
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
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Damien Bonne*
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
,
Jean Rodriguez
Aix Marseille Université, CNRS, iSm2 UMR 7313, 13397 Marseille, France   Fax: +33(491)289187   Email: damien.bonne@univ-amu.fr   Email: xavier.bugaut@univ-amu.fr
› Author Affiliations
Further Information

Publication History

Received: 28 February 2013

Accepted after revision: 03 May 2013

Publication Date:
03 June 2013 (online)

Abstract

Several reactive sites of 1,2- and 1,3-ketoamides were successively exploited in two complementary domino transformations for the synthesis of polysubstituted monocyclic or bridged bicyclic cyclohexanes, with the creation of up to six stereogenic centers. In both cases, a chiral bifunctional thiourea organocatalyst allowed efficient control of chirality in the final carbocycle.

Supporting Information

 
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