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The direct conversion of carbamates to ureas using aluminum amides

Sang-Hyuep Lee, Hana Matsushita , Bruce Clapham* and Kim D. Janda

*Department of Chemistry, The Scripps Research Institute and The Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Email:

S.-H. Lee, H. Matsushita, B. Clapham, K. D. Janda, Tetrahedron, 2004, 60, 3439-3443.

DOI: 10.1016/j.tet.2004.02.034


Carbamates can be converted into ureas using aluminum amide complexes. Bi-, tri- and tetra-substituted ureas were prepared from carbamate-protected primary or secondary amines by reaction with primary or secondary amines in the presence of stoichiometric quantities of trimethylaluminum. Methyl and benzyl carbamates were reacted selectively in the presence of t-butyl carbamates.

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Key Words

Ureas, Carbamates, tert-butyl carbamates, Lewis acids

ID: J72-Y2004-450