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Synfacts 2014; 10(12): 1284
DOI: 10.1055/s-0034-1379593
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Asymmetric Intramolecular Cyclopropanation

Contributor(s):
Hisashi Yamamoto
,
Ramesh C. Samanta
Shen J.-J, Zhu S.-F, * Cai Y, Xu H, Xie X.-L, Zhou Q.-L. Nankai University, Tianjin, P. R. of China
Enantioselective Iron-Catalyzed Intramolecular Cyclopropanation Reactions.

Angew. Chem. Int. Ed. 2014;
DOI: 10.1002/anie.201406853
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Publication History

Publication Date:
18 November 2014 (online)

 
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Key words

spiro-bisoxazolines - cyclopropanes - iron

Significance

An enantioselective intramolecular cyclopropanation using catalytic iron(II) with a chiral spiro-bisoxazoline ligand is presented. This reaction demonstrates the potential abilities of iron in asymmetric carbenoid transformation reaction.


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Comment

The superiority of the iron(II) complex over precious metals in this reaction is the most important finding. However, the enantioselectivity is strongly affected by the steric hindrance through the α-diazo ester and the substituents of the alkene. Due to the rapid change of the oxidation state of the iron complex the mechanistic study turned out to be difficult, and no direct mechanistic evidence has been depicted.


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