Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles

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

Key words

organocatalysis - domino reactions - multicomponent reactions - cyclohexanes - cyclohexenes - asymmetric synthesis

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