Iron-Catalyzed Asymmetric OH Bond Insertions

doi:10.1055/s-0030-1258689

Synfacts 2010(10): 1143-1143
DOI: 10.1055/s-0030-1258689

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Iron-Catalyzed Asymmetric OH Bond Insertions

Contributor(s):Hisashi Yamamoto, Zhi Li

S.-F. Zhu, Y. Cai, H.-X. Mao, J.-H. Xie, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
Enantioselective Iron-Catalysed O-H Bond Insertions
Nat. Chem. 2010, 2: 546-551

Abstract

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Key words

spirobox ligands - OH insertion - α-diazophenylacetates - iron

Significance

The authors developed a highly efficient iron-catalyzed protocol for the enantioselective carbene OH insertion. The reaction produces various α-alkoxy and α-hydroxyl arylacetates, which are quite useful synthetic intermediates, in very high yield and enantioselectivities.

Comment

This work features not only the high efficiency of iron-catalyzed carbene insertion to alcohol OH bonds, but also the insertion to a water OH bond to generate corresponding chiral α-hydroxyl arylacetates in high yields and enantioselectivities. The results are better than the authors’ previous work with copper catalysts (Angew. Chem. Int. Ed. 2008, 47, 932).

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