Synlett 2015; 26(02): 142-166
DOI: 10.1055/s-0034-1379251
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 21 July 2014

Accepted after revision: 15 September 2014

Publication Date:
17 December 2014 (online)


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