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Synfacts 2014; 10(1): 0082
DOI: 10.1055/s-0033-1340370
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Zn/Cu-Mediated Aminocyclopropanation

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Ishikawa S, Sheppard TD, D’Oyley JM, Kamimura A, Motherwell WB * University College London, UK and Yamaguchi University, Ube, Japan
A Rapid Route to Aminocyclopropanes via Carbamatoorganozinc Carbenoids.

Angew. Chem. Int. Ed. 2013;
52: 10060-10063
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

cyclopropanation - zinc - copper

Significance

The authors report a novel method for the preparation of carbamate-protected aminocyclopropanes. The reaction proceeds via aminocyclopropanation of alkenes using carbamates in the presence of metallic zinc and copper. The conditions are very mild (room temperature) using only 3.2 equivalents of carbamate.


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Comment

The prepared cyclopropane carbamates can be deprotected using iodotrimethyl­silane in chloroform and methanol. Subsequent ­isolation furnishes the corresponding aminocyclopropanes as their crystalline HI salts in high yields.


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