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

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

lanthanides - samarium diiodide - catalysis - enantio­selectivity - carbon-nitrogen bond formation

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