Synthesis 2013; 45(14): 1909-1930
DOI: 10.1055/s-0033-1338484
review
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles

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

Publication History

Received: 18 February 2013

Accepted after revision: 08 April 2013

Publication Date:
06 June 2013 (online)


Dedicated to the elegant and stimulating realizations of Professor D. Enders in the field of this review

Abstract

Polysubstituted chiral cyclohexanes and cyclohexenes are important building blocks in organic synthesis. From historical and pioneering reports to the most recent accounts, this review focuses on domino enantioselective organocatalytic methodologies that have allowed the control of the relative and absolute configurations of up to six stereogenic centers in the construction of these versatile molecular architectures.

1 Introduction

2 Two-Component Transformations

2.1 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds

2.2 Michael-Initiated Domino Reactions with Nitroolefins

2.3 Non Michael-Initiated Domino Reactions

3 Multicomponent and Related Transformations

3.1 Pseudo-Three-Component Reactions

3.1.1 Michael-Initiated Domino Reactions with Nitroolefins

3.1.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds

3.2 Consecutive Reactions

3.2.1 Michael-Initiated Domino Reactions with Nitroolefins

3.2.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds

3.3 Multicomponent Reactions

3.3.1 Michael-Initiated Domino Reactions with Nitroolefins

3.3.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds

4 Conclusion