Synlett 2009(13): 2051-2067  
DOI: 10.1055/s-0029-1217511
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Samarium Iodides: Catalysts for the Formation of Carbon-Nitrogen Bonds

Jacqueline Collin*, Sophie Bezzenine-Lafollée, Richard Gil, Nada Jaber, Myriam Martin, Iréna Reboule
Equipe de Catalyse Moléculaire, ICMMO, UMR 8182, Université Paris-Sud, 91405 Orsay, France
Fax: +33(1)69154680; e-Mail: jacollin@icmo.u-psud.fr;
Further Information

Publication History

Received 23 December 2008
Publication Date:
23 June 2009 (online)

Abstract

Lanthanide iodides offer great reactive scope as Lewis acid catalysts. Samarium diiodide allows a wide range of carbon-carbon bond-forming reactions, such as Mukaiyama aldol, Diels-Alder, or tandem Mukaiyama Michael aldol reactions. Moreover, lanthanide iodides exhibit high catalytic activities for carbon-nitrogen bond formations which are reviewed here. Highly enantio­enriched amino alcohol and amino acid building blocks are obtained thanks to a new family of enantioselective catalysts developed in our laboratory, iodolanthanide binaphtholates.

1 Introduction

2 Samarium Diiodide Catalyzed Reactions with Formation or Cleavage of Carbon-Nitrogen Bonds

2.1 Ring Opening of Epoxides with Nitrogen Nucleophiles

2.2 Aza-Michael Reactions

2.3 Transformation of N-Acyloxazolidinones into Esters

3 Enantioselective Formation of Carbon-Nitrogen Bonds with Lanthanide Iodides

3.1 Preparation of Chiral Lanthanide Iodides and Enantioselective Catalysis of Carbon-Carbon Bond Forming Reactions

3.2 Enantioselective Aminolysis of Epoxides

3.3 Enantioselective Aza-Michael Reactions

4 Conclusions

10

Dinut, A.; Gil R. unpublished results.