Synfacts 2008(9): 0964-0964  
DOI: 10.1055/s-2008-1078004
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pincer-type Ligands for Enantioselective Catalysis

Contributor(s):Hisashi Yamamoto, Joshua P. Abell
B. K. Langlotz, H. Wadepohl, L. H. Gade*
Universität Heidelberg, Germany
Chiral Bis(pyridylimino)isoindoles: A Highly Modular Class of Pincer Ligands for Enantioselective Catalysis
Angew. Chem. Int. Ed.  2008,  47:  4670-4674  
Further Information

Publication History

Publication Date:
22 August 2008 (online)


Significance

In transition-metal catalysis, iron-containing complexes still remain a largely undeveloped field of chemistry. The authors demonstrate a simple, highly modular pincer-derived ligand which showed moderate to high enantio­selectivity for iron-catalyzed hydrosilation and cobalt-catalyzed cyclopropanation. The synthesis of the ligand is rather straightforward and this system may have further application in the future.

Comment

Controlling the direction of nucleophilic attack seemed problematic with previously reported pincer-derived ligands. The authors solved this problem by designing a highly modular and tunable ligand which, by X-ray crystal structure analysis, is a distorted octahedral complex. With the highly sterically encumbered pincer ligand the authors were able to control the backside attack of the active site of the catalyst.