Synlett 2010(2): 174-194  
DOI: 10.1055/s-0029-1219157
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Phosphine Organocatalysis

Angela Marinetti*, 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; e-Mail:;
Further Information

Publication History

Received 28 July 2009
Publication Date:
22 December 2009 (online)


The broad potential synthetic usefulness of phosphine-promoted reactions has stimulated many recent investigations on enantioselective variants of known reactions of this family, as well as the search for new, specifically designed, chiral phosphorus catalysts. This short overview summarizes the state of the art in this field and highlights the most significant achievements, with special emphasis on our recent work.

1 Introduction

2 Chiral Phosphine Organocatalysts

2.1 Cyclic and Bicyclic Phosphines

2.2 Acyclic Phosphines with Hydrogen-Bonding Functionalities

3 Enantioselective Phosphine-Promoted Reactions

3.1 Acylation of Alcohols and Other Acyl-Transfer Reactions

3.2 Morita-Baylis-Hillman-type Reactions

3.3 [3+2] and [4+2] Cyclizations between Allenes and Imines

3.4 [3+2] Cyclizations between Allenes and α,β-Unsaturated Ketones and Esters

3.5 Addition of Nucleophiles to Unsaturated Electron-Poor Substrates

3.6 Allylic Substitutions on Morita-Baylis-Hillman Adducts

3.7 Miscellaneous Reactions

4 Summary and Outlook