Phosphine Organocatalysis for the Synthesis of Spirocyclic Compounds

Arnaud Voituriez; Angela Marinetti; Maxime Gicquel

doi:10.1055/s-0034-1379251

Synlett, Table of Contents

Synlett 2015; 26(02): 142-166
DOI: 10.1055/s-0034-1379251

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Phosphine Organocatalysis for the Synthesis of Spirocyclic Compounds

Arnaud Voituriez*

Institut de Chimie des Substances Naturelles, CNRS UPR 2301, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Fax: +33(1)69077247 Email: arnaud.voituriez@cnrs.fr Email: angela.marinetti@cnrs.fr

,

Angela Marinetti*

Institut de Chimie des Substances Naturelles, CNRS UPR 2301, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Fax: +33(1)69077247 Email: arnaud.voituriez@cnrs.fr Email: angela.marinetti@cnrs.fr

,

Maxime Gicquel

Institut de Chimie des Substances Naturelles, CNRS UPR 2301, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Fax: +33(1)69077247 Email: arnaud.voituriez@cnrs.fr Email: angela.marinetti@cnrs.fr

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Abstract

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Abstract

This account describes the use of phosphines as simple organocatalysts that catalyze the synthesis of complex spirocyclic compounds. Besides our own results, coverage of relevant literature in this field is also provided, including asymmetric variants and synthetic applications.

1 Introduction

2 Cycloaddition Reactions Involving Allenoates or 2-Butynoates

2.1 [3+2] Cycloadditions

2.2 [4+2] Cycloadditions

2.3 [4+1] Cycloadditions

3 [3+2] Cycloadditions with Morita–Baylis–Hillman Adducts

4 Cycloaddition Reactions Using Ynone Derivatives

5 Cycloaddition Reactions Involving Methyl Vinyl Ketone

Derivatives

6 Miscellaneous Reactions

7 Conclusions

Key words

phosphines - organocatalysis - enantioselective catalysis - spirocyclic compounds

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References

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