Collect. Czech. Chem. Commun. 2007, 72, 1697-1706

Synthesis of N-[(3-Amino-1,2-dicarba-closo-dodecaboran-1-yl)acetyl] Derivatives of α-Amino Acids

Galina L. Levita,*, Victor P. Krasnova, Dmitriy A. Gruzdeva, Alexander M. Demina, Iliya V. Bazhova, Liliya Sh. Sadretdinovaa, Valentina A. Olshevskayab, Valery N. Kalininb, Chan Seong Cheongc, Oleg N. Chupakhina and Valery N. Charushina

a Postovsky Institute of Organic Synthesis of Russian Academy of Sciences (Ural Division), 620041 Ekaterinburg, Russian Federation
b Laboratory of Fine Organic Synthesis, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation
c Life Sciences Division, Korea Institute of Science and Technology, 130-650 Seoul, Korea


The N-[(3-amino-1,2-dicarba-closo-dodecaboran-1-yl)acetyl] derivatives of α-amino acids were prepared starting from N-protected (Ac, Form, Bz, and Boc) 3-amino-1-(carboxymethyl)-o-carboranes and alkyl esters of natural α-amino acids using the carbodiimide method of coupling and removing the ester groups. All the amides obtained were diastereoisomeric mixtures. Some diastereoisomers were separated and the assignment of the absolute configuration of aminocarborane fragments was performed by X-ray crystallography.

Keywords: Amides; N,N'-Dicyclohexylcarbodiimide; Amino acids; Carboranes; Diastereoisomeric resolution; HPLC; NMR spectroscopy; X-Ray crystallography.

References: 7 live references.